Trash my closet and start over? I don't know how to dress myself.
January 15, 2014 11:16 AM   Subscribe

It's embarrassing to admit to being a 33 year old woman who can't dress herself, but my frustration is outgrowing my embarrassment. I have pretty much nothing in my closet that I like to wear, and that I feel I look good in. I wear nearly the same thing every day: jeans, sneakers/tennis shoes, t-shirt or slightly fancier t-shirt, and one of several ratty hooded sweatshirts, each of which has a hole in the left elbow. I dress like slob. I do not feel this look suits me, and I want to change it, but don't know how.

There are a number of issues which are contributing to this sad state:
1. I have no understanding of the basics of putting together an outfit, a style, shopping correctly, etc.

These are likely skills that should have been imparted growing up, but for various reasons, I missed those lessons. I've tried to research this on my own. I've read how-tos, searched the intrawebs, and even discovered /r/femalefashionadvice on Reddit, and I haven't been able to integrate any of that knowledge in a useful fashion. That subreddit skews very young—though I am not interested in looking, well, old—and is not useful in the way that a manual on a given programming language won't be useful to someone that doesn't understand the basics of programming.

2. I am *literally* unable to visualize what something would look like on me, and I have some unpleasant shopping anxiety.

I am tall, with narrow hips, and am relatively thin. I feel as if most clothes are made for women with some curves, and fit me poorly. I can't tell if something would or would not look good. If I try it on, maybe, but due to some longstanding body and self-image issues, my automatic expectation is that it'd make me feel awful, even though I know my overly critical view of myself is unrealistic and biased. This makes online shopping hard, but also in-store shopping, since I can't even decide what to try on. In the past, I literally relied on having best friend pick out my clothing. I don't live near her anymore, and I don't have any female friends whom I could ask for help.

Clothes shopping in general fills me with anxiety, and I am not able to think about the task at hand, and I get to the point where I am in a rush to just leave, even if I have only been in the store a few minutes.

3. Everything seems really expensive, even if it's not.

I grew up dirt poor. I have been very poor my whole life, until recently, where I somehow arrived at a middle class income. This history has colored my perception of money and value. I don't know what the "normal" price for anything is. Paying $100 for a pair of shoes, or $300 for a purse or dress or whatever seems highly extravagant, though I get the impression this isn't the case. I have a lot of $10 t-shirts from Target. The most I've ever paid for jeans is $30, and I felt guilty doing it.

I could budget out a few hundred a month to update my wardrobe, if I wanted, so I think this kind of fear of spending is going to hinder me more than help me, but it is kind of ingrained.

4. I don't know what I want to wear or what kind of style I want.

I used to dress goth, until my early 20s. It was easy, and there were no scary uncertainties, as it only required long black skirts, ripped up black jeans, black t-shirts or lacy black tops. This probably didn't look good, but at least I didn't have to think about it. Currently, I don't even know what I want. I mostly never notice what other people are wearing. If I do, and it looks good, what I am most likely to think of is how it wouldn't fit on me, etc.

I have mostly shopped out of the juniors section of a given store, as the jeans were more likely to fit, but lately, regardless of the store this stuff has all seemed really juvenile. On the other hand, the "adult" women's section seems almost the opposite extreme, like things I'd expect to see on an elderly person, or soccer mom (no offense to either groups meant). Bright, garish patterns that could be some kind of BLIT, and gross feeling fabrics. I want to feel attractive without coming off as trying to be a teenager, I suppose. I have nice legs, but don't own any skirts. I am self-conscious about my figure but it's objectively not bad. I own no jewelry. I don't know what to do with any of this.
I basically have never been able to overcome any of this, and as such I kind of "missed out" on some things. My body is no different than it was 10 years ago, so I'd like to make the most of what I put on it before things start sagging, fat starts accumulating in weird places, or my head caves in or whatever. This is all really overwhelming, and what I would like most is some kind of formula where I put in my measurements and the result is "Buy this item of clothing and wear with this item of clothing and these shoes. Now do this for each color you don't hate." This doesn't exist.

What do?
posted by polywomp to Clothing, Beauty, & Fashion (67 answers total) 75 users marked this as a favorite
I think you might benefit from an appointment with a personal stylist, such as the Nordstrom program. Even if you don't buy much during the trip (they are happy to work within any reasonable budget), you will still get an idea of what looks nice on you, what makes you happy to wear, and what "look" you might like best. Be prepared to try on a LOT of clothes - it will be exhausting, but rewarding.
posted by schroedingersgirl at 11:26 AM on January 15, 2014 [4 favorites]

Best answer: If you have some real money to throw at this, I would consider signing up for a personal shopper/stylist session at a department store. I know Nordstrom's has this kind of service, but I am sure others do as well. Go once, and learn mightily!

Another idea: select a color palette you like and buy stuff in that palette only. It sounds limiting, but it's actually quite freeing because when you shop, you don't get bogged down in the sheer quantity of stuff. You look for things that are your colors, and then mixing and matching gets easier as well.

Personally, I've recently treated myself to a monthly delivery service called StichFix. With $20/month and a decently completed profile, they send me 5 items I can try on and keep or return as needed. There is a time-limit, so you have to return things quickly, but the $20 goes towards anything you decide to keep. I L-O-V-E this, because I dislike shopping in stores and using dressing rooms, and so far, I am a believer in their stylists. It's been a LOT of fun. But individual pieces are closer to $75 than $25 in general.

Prices in my suggestions above are going to be hard for you to adjust to, I think, and that's understandable. However, buying nice pieces for more money has made me feel way more put together and keeps my wardrobe reasonable/manageable, so I'm not overwhelmed when I dress each day. And the items last longer, too.
posted by juliplease at 11:26 AM on January 15, 2014 [12 favorites]

Best answer: 2. I am *literally* unable to visualize what something would look like on me, and I have some unpleasant shopping anxiety.

How would you feel about taking a trip to a major department store and committing to JUST TRYING THINGS ON. Like, you don't have to buy anything. You just need to try stuff on. Can't decide whether you should try something on? Try it on! I mean seriously. Commit to trying 20 things on. Don't worry about how much they cost. You are just trying things on. Do five items or outfits at a time. Maybe you'll start to notice some trends in what you like. Maybe you take some fitting room selfies and send them to your friend who used to help you?

Have you ever watched the show What Not To Wear (I'm thinking of the US version but I suspect the UK version is similar)? At some point in every episode the person who's getting made over is standing around, lost, in Macy's or whatever, and then they swoop in with an armful of clothes and make her try them on, even though she's like, "I don't think that would look good on me!" and (admittedly with the help of reality-tv editing), inevitably she finds something she likes in that armful of clothes.

Also: you can buy your jeans in juniors and your tops from the grownup ladies department. Ask me how I know!

And: maybe you would benefit from the services of a personal shopper. I know that sounds like EVEN MORE MONEY but this is causing you great distress! If you can afford to throw some money at the problem and fix it quickly, go for it.
posted by mskyle at 11:26 AM on January 15, 2014 [2 favorites]

I went through this process in the two years. I actually just put together some links to things that I found wildly helpful here.
posted by Nimmie Amee at 11:28 AM on January 15, 2014 [11 favorites]

What are you dressing for? In what kind of environment do you spend most of your days? One thing you could do is look around at others in said environment and take note (on pen and paper, if necessary) of outfits that look good to you, items that seem appealing, and what makes an outfit seem to work or not work.

For example, when I started working at an office right after college, I had zero "business casual" clothes and took cues from my female coworkers and other women I'd see downtown around my office building. Then, when I was shopping, I'd remember that I actually hate how this or that skirt looks, or that I saw someone wearing a fetching blue sweater that I liked, and seek out/avoid similar.

Something I used to do when I was younger (teens-early 20s) and still figuring out my style was to take cues from female characters in movies and TV shows, and have them in mind when I was out shopping--I'd select items that looked like what [Julie Delpy in Before Sunset, for example] would wear, and try it on to see if it worked for me. That helped me pinpoint some of my aesthetic preferences, and I wasn't beholden to any brand or department store. The strategy works pretty well in thrift stores or anywhere, really.
posted by magdalemon at 11:31 AM on January 15, 2014 [3 favorites]

Best answer: I do not feel this look suits me, and I want to change it, but don't know how.

Would it be possible to post a few photos of some looks you like, maybe on celebrities? It can be a variety of different kinds of looks.

Or if nothing like that comes to mind right now, maybe some adjectives would help? For example, if I were to describe how I like to look normally, it would be something like sporty/preppy/hippie/surfer girl. If I were to describe how I like to look at work it would be something like expensive casual/trendy/yuppie. (Where I live/in current my line of work people wear $300 t-shirts to work. So I like to look like that too even though in reality I feel ethically wrong paying that much for clothing.)

About the budget stuff. $100 for shoes is on the extravagant side. If you are getting really high quality shoes that will last you a while, I think that it is reasonable. But you can get good quality new shoes in the $50-100 range as well.

Up to $80 or so is typical for new jeans. That's why I don't ever buy new jeans.

$300 for a dress is VERY extravagant. A nice dress will usually cost $40-$100, casual dresses should be under $40. I would never, ever buy a purse for $300. That is very extravagant. Take a look at the Macy's website. Macy's is not the most fashion-forward store BUT everything they have is being sold for average/reasonable prices so it will give you a good idea of what average/reasonable prices for different things can be.
posted by cairdeas at 11:32 AM on January 15, 2014

Seconding a lot of Nimmie Amee's links; I came in here to list YouLookFab and Already Pretty as resources for you to read in advance of a try-on trip to give you some ideas about your style.
posted by immlass at 11:33 AM on January 15, 2014 [1 favorite]

How tall is tall? Do you need "tall" clothes or do you wear average cuts? This will change the advice you get.

1. I would suggest looking at lots and lots of body-positive selfie-oriented tumblrs, not with a view to picking anything out but just with a view to desensitizing yourself to pictures of women in clothes - getting so that thinking about clothes does not produce an automatic "I am going to look so terrible". Seeing many pictures of regular women in clothes has helped me a lot with this.

2. Maybe set a small goal that is not too overwhelming? Like, you are going to buy X number of new fashion items of all sorts; or you are going to replace three shirts; or you would like to have a dress. "I would like to buy three shirts and I would like them to be blue and I would like them to be casual" is a lot easier than "I would like some kind of random new wardrobe".

3. Also maybe consider this an intermediate step? Like, you're going to get a few new things now so that you can try them out, and in the long run this will clarify how you want to dress, but you do not need to buy The Ten Important Wardrobe Items That It Is Worth Spending Lots Of Money On right now or whatever - you can just buy a few moderately priced separates and figure out which ones work.

4. Where do you usually shop? Target? Department stores? That's precisely where you're going to find the gross fabrics and really age-polarized garments. If you focus on stores that routinely clothe women in their twenties - forties, you'll have better luck - in a mainstream sense, why not JCrew/Ann Taylor/Gap/similar? You don't need to put together a "J Crew style" outfit - you can just pick up a really nice pair of black pants.

5. Some things are worth spending a lot of money on and some are not. I would not suggest buying a really expensive bag or shoes unless you know your own taste and really can buy for the long haul.

6. Don't shop clearance unless you have a clear vision - it is very easy for the parsimonious and confused to end up with a closet of weird clothes that were originally expensive, marked way down and don't fit right. (Ask me how I know!)

7. I tend to pick my clothes (and I am ultra fussy) based on these questions: What are my favorite colors? Do I like patterns? What materials and textures do I like? How much energy do I want to put into washing this? What will I wear it for? So basically, almost all my clothes are blue/grey/violet/black in solids or simple patterns; they are almost all cotton, machine washable and require little ironing; and all of them can be worn while riding a bike and at a business casual job. Every day, pretty much, I wear a button front shirt and pants. In winter I add a cardigan and scarf. I wear loafers in the summer and boots in the winter. (It's sort of a men's style blogger look, actually.) I never iron.

8. I picked my bag based on [sad failure with lots of unsuitable bags] how I use bags: I carry a lot of stuff, I often stop at the grocery store, I am always pulling stuff out of my bag while wearing it (so no backpack) and I lose stuff easily (so external pockets for keys, phone and wallet). Then I applied the natural fibers and blues/greys filters. So I have two iterations of this bag, both secondhand.

9. To get things to fit, you do have to try them on, lots of them. But a way around this is to take baby steps - let's say you want a blue cardigan but you don't want to try on a ton of them. Try on several, buy the won't fit perfectly, but it will be okay. Think about how you'd like it to fit differently, then bring that to bear on the next cardigan you buy.
posted by Frowner at 11:37 AM on January 15, 2014 [3 favorites]

First of all, it's okay! You're 33. You have more than half of your life in front of you statistically speaking so this is a great time to learn how to dress yourself. You're tall, thin and don't have hips? You sound like you're built like a model.

Start by identifying what colors look good on you and what colors you like to wear. Here's an easy thing you can do - black and white with an accent color. I have a white sweater with black dots. I wear that with a pair of black pants and a big red necklace and I feel like I look pretty good.

I know what you mean with regard to money but it becomes easier to deal with the more that you face it. It's hard to believe coming from the perspective of someone who's been dirt poor but investment clothing purchases are cheaper over the long haul. My black leather boots were around $100 when I bought them. They've lasted four years with occasional polishings. I think that's not bad, considering how much I wear them, and I love them.

I agree that trying a personal shopper at Nordstrom's would be a great place to start. I also think that upping the stuff you already wear would be a good idea. You wear sneakers - what about a pair of loafers or ballet flats instead? How about wearing a cardigan sweater or a jacket over your t-shirt instead of a hooded sweatshirt?

I would look at some fashion blogs just to get a feel for things you like and don't like. Pinterest would also be helpful for this. I like this blogger because the stuff she wears is cute and not expensive, though I can't wear most of the items she wears. You don't have to spend a lot of money to look good. I think I look okay generally and for the last two days in a row, everything I've worn has come from Target (and I bought it on sale).

Good luck and have fun!
posted by kat518 at 11:38 AM on January 15, 2014

Best answer: Step 1 that worked for me is discarding (donating) EVERYTHING with stains, frays, and holes. This includes underwear. If throwing stuff out upsets you, you can put the non-donatable things into textile recycling. You have to tell yourself: if you had it in you to mend the hole properly, wouldn't you have done it by now?

Step 1 is easy because it's a binary choice: is there, or is there not, a hole?

If you have a friend to strengthen you in this, now's the time to ply him/her with refreshments in exchange for help.

Step 2 is almost completed, but I still have some holdouts. Donate EVERYTHING you dislike. Even if your mother or late grandmother gave it to you, even if you bought it at a particular store in your old hometown, even if OTHER PEOPLE like it on you, even if it was a good deal...

After this you should have, let's say, 3 days' worth of clothing about which you feel neutral. Maybe even 1 or 2 positives.

Step 3 is to get new stuff at an affordable price...I'm not there yet.
posted by skbw at 11:41 AM on January 15, 2014 [10 favorites]

I can't speak to the anxiety aspect, but my favorite "style basics" blog is Putting Me Together--the blogger is 30ish, and she has tons of $10 shirts from Target too! But she does a great job of explaining the process of building a wardrobe from scratch, deciding what pieces to buy for your lifestyle and personal needs, etc. There are also a lot of posts that show a basic outfit of, say, cardigan + shirt + jeans + boots, with tips on styling and links to several different options for each piece. Her style is not too girly or fashion-y, just simple and put together.

Good luck!
posted by sunset in snow country at 11:41 AM on January 15, 2014 [9 favorites]

Before you start worrying about shopping, it would be a good idea to try to form some more ideas of what you might like or how you would like to look. Magazines are OK, but the clothes are generally more spiffy and special--and more expensive--than you probably are interested in. But you can still get an idea of some general looks that appeal to you. Tear out pages with pictures of women that appeal to you, even if you don't actually intend to buy those clothes or try for that particular look. Just pictures that appeal, for whatever reason. Then you can muse over the pictures and try to identify why you like it. Maybe a particular item of clothing does appeal to you; maybe the model has a general demeanor that you like, and her clothes are helping to create that demeanor.

In real life, look around and try to notice other women and what they're wearing. What kind of places/activities are you looking to dress for? What kind of workplace do you have? I imagine it's quite casual if you wear jeans, t-shirts, and holey hoodies. Are there other women there? Look at how they dress, if it's different than you. Are there any women that you think look nice or project an image or type of look that you like or would like to also project? Try to notice the details of their clothes; even ask them. Most people are very flattered if you tell them you like their outfit or a particular item and ask where they got their clothes. Do you go out at night to bars or clubs? Again, look at the women that appeal to you in those places and notice how they dress. Check out other women on the street, in stores, restaurants, wherever you go, trying to focus on WHY you like the way the look. In the meantime, check out The Gap and maybe try stretching a little from your current style and just push the boundaries a little. Try corduroys or khakis in addition to jeans. Try a nice, plain button-down over a tee or instead of a tee. Try a cardigan instead of a hoody. Try different shapes of pants and tees or sweaters there to see what silhouette works on you.

This may take a while, trying to identify what you like, but I think it's important before you start actually shopping. When you do feel ready, it might be helpful, just in the beginning, to go to a larger department store, like Nordstrom's, that has personal shoppers. They can be very helpful in figuring out what styles flatter you or don't, as well as helping you translate how something looks on a hanger into how it might look on you. You don't need to continue to shop at that particular store, but use the shopper as a tool to help you move forward at other stores. I have a feeling that stores like The Gap might be a good match for you; straightforward, unfussy basics, including work wear.

Also: #2: your clothing budget sounds generous. More than enough for maintaining a wardrobe once you've built it up, and #3: The clothing industry uses just your type of body as a model: tall, thin, straight rather than curvy. Except in certain clothing lines, perhaps, your body type should not be a particular problem.

And please remember, just because you're a woman doesn't mean you have to love clothes or even care about them at all. Just aiming for decent fit, cleanliness, and no holes might be just enough for you.
posted by primate moon at 11:42 AM on January 15, 2014 [1 favorite]

All the options out there are overwhelming and daunting. But I really strongly believe that anyone can look far more presentable simply by wearing nicely made clothes (meaning, in good condition, well constructed of mostly natural fibers) that fit properly.

Seriously. If you just have a dozen or so nice basic pieces that fit you (or you get tailored to fit you), you are 90% of the way there. Work on the basics first; don't stress yourself out thinking everything has to be perfectly accessorized and completely true to your personal style and blogger-worthy right away. You could simply replace your sweatshirts with a more refined outer layer (like a cardigan, blazer, or leather jacket) and already feel vastly more polished. Then maybe in a month or two you can think about replacing the sneakers with something different (flat boots, ballet flats, driving loafers, whatever you like and are comfortable in). And so forth.

I'm a big fan of J. Crew, and they have tall sizes and their clothes are not cut for super-curvy women. I also find that most of their clothes are reasonably priced for the quality, especially if you wait for a sale. They have a personal shopper service, and you could pretty much leave it in their hands.
posted by payoto at 11:43 AM on January 15, 2014

You are tall (taller than 5'9"?), and relatively slim you say? well there's a place for you: Jcrew. (they do tall sizing through the internets and it's magnificent) don't like being preppy? take a look at Madewell or Gap. Jeans wise, I love Levi's- and they run closer to $60 for a new pair of pants and have a sizing system that kind of does make sense.

now how to approach this.....

first spend 1 day emptying your closet of anything ripped, stained or very unflattering. (you know that shirt you won't even wear on laundry day, but keep just in case? yea get rid of it). also get rid of any single socks, and weird uncomfy underwear.


I would start with switching out your hoodie to a blazer and getting a new pair of jeans. This lets you keep your old t-shirts/current uniform but slowly upgrades it.

In the spring, buy a pair of flats. now you're wearing newish jeans, a blazer, comfy old t-shirt and niceish shoes.

In the summer, try on a necklace, and flip your t-shirt to a tank top. still got your (now) old jeans, blazer (if it's cold), tank top, but working in some jewelry.

and in fall, back to t-shirt, blazer, jeans, keep the flats and then switch out the necklace for a scarf. refresh your jeans. maybe get a few new t-shirts.
posted by larthegreat at 11:45 AM on January 15, 2014 [9 favorites]

Just for what it's worth--your impression that "clothes are made for curves" is pretty inaccurate. In fact, most clothing is made to look good on models, mannequins, and hangers, none of which are notable for their big boobs or curvy hips.
posted by like_a_friend at 11:46 AM on January 15, 2014 [12 favorites]

Do you have any stylish friends that you trust? A friend and I together formed a style team for a third friend who was in a very similar situation to you — he's color blind and always assumed that he'd never be stylish, would never have an eye for it, etc.

I don't think I could have told you beforehand what would look good on him, but being there and sending him into the dressing room with piles of stuff did the trick. We found a style for him that he really liked and that he continues to build on to this day. Having the initial foundation really helped him — he picks things out himself now that are awesome.

I would start with a single, big shopping trip with a friend or a personal stylist/shopper. Set a budget of $X00 for that trip. Buy a bunch of basics that feel good — tops pants skirts shoes — and a few exciting things — fancier dress, awesome coat. Live with them for a while. See how they feel on, see how you feel in them. Some things are going to feel wrong a month later, some so so right.

It's a process of learning what you like and what feels good on. If you can get help in the first step of the journey you'll be well on your way.
posted by wemayfreeze at 11:46 AM on January 15, 2014

Hi! I was you for a long time and still am a little bit. I'm slowly learning what I like, what things will look good on me, and how to put some basic types of outfits together. The only thing that got me here was seeking out help from a personal shopper. DEFINITELY go to Nordstrom and make a (free!) appointment with one. You're under no obligation to buy anything, but definitely give yourself permission to splurge on one or two items if they really make your heart flutter.
posted by joan_holloway at 11:48 AM on January 15, 2014

Lots of practical advice here already, so I'll try emotional advice; pulling together a "look" is nice, and can even be fun, but it is not something to really stress out about. Unless you are dressing really outrageously, you merely look like a regular woman to everyone else. Women's magazines and cable shows excel at making us feel bad/dowdy/wrong/unstylish if we don't look completely pulled together at all hours of the day, but that's bullshit. Very few people have the time and money to always be coordinated, and most of them hire people to do it for them. Because it's hard! So let yourself off the hook a bit. You're not running around naked. You are at present adequately clothed. You just want to take it up a notch.

Somewhere in your closet, or in your past, there is an item of clothing you liked or even loved. Think about that item. Was it a certain color? Fabric? Cut a certain way? Had a type of useful pocket? I loved a red-and-purple shirt with an apple on it when I was a kid, which I wouldn't wear now, but, I still love that shade of purple and buy grownup clothes that have it on occasion. I once had a chenille sweater that felt amazing, so I gravitate towards clothes that have that texture. Etc. There is something you like out there, that you can use as a building block/starting point. Try to wear things that make you feel good, even if it's grownup/office versions of those things. Along they way, you will discover other things that make you feel good/look good, and they'll become part of your look.
posted by emjaybee at 11:48 AM on January 15, 2014 [2 favorites]

Best answer: Hm. I'm going to go against the grain a little here. Sounds to me like you're not that interested in clothes, and you're also discriminating and minimalist. (I say that because you say garish patterns irritate you, you don't want to look either young or old, and you don't own jewelry.)

Given that, I don't think a personal shopper or reading a lot of blogs is going to help you much. Personal shoppers *like* clothes, and are into fashion -- they can dress you up once, but you won't learn anything, and I'm guessing you'll find it boring and frustrating. They're also fundamentally sales people: their interests aren't the same as yours. Essentially the same thing is true for fashion blogs. They are written by people who love playing with clothes, and you are not one of those people.

I think you should focus on building a wardrobe of basics, slowly over time. Buy less, and buy better quality. If I were you, I'd go somewhere like Bloomingdale's or Neiman Marcus, and take a look at brands like Theory, T by Alexander Wang, maybe Michael Stars, Velvet, and Rag and Bone. That's more money than you're used to paying, but the upside is it takes out a lot of the guesswork. Fabric and cut will be better than cheap brands, there will be less extraneous foofery, and the clothes will feel better on your body, hang better and last longer. Maybe also try quality "active" brands like Icebreaker and Smartwool.

If you do that for a while, I'm guessing eventually you'll start to figure out what you like, and what suits you.
posted by Susan PG at 11:50 AM on January 15, 2014 [17 favorites]

I had to laugh, Tall with narrow hips is EXACTLY who clothes are designed for! You lucky, lucky woman!

Being able to suss out good buys at Target is for the shopping advanced, so resolve to select a good department store (I recommend Macy's) and stick with it. This will help the shopping anxiety stay in the background.

I never buy anything at full retail price. Macy's has coupons in the paper and I try to shop on sale days. I just bought a black and white skirt for $8.00. You don't have to pay a fortune.

1. Get fitted for a bra. You will pay through the nose, but once you have your foundation garments sorted out, fitting your clothing will be SO MUCH easier! I promise. Do go to Nordstrom for this. They have the best bra fittings. You only need one or two good bras. Not one for each day. Buy the cleaning stuff and rince them out in your sink.

2. Study this list from Tim Gunn. It's a good starting place. Tim Gunn's 10 Essential Basics.

3. If you like black, make it the foundation of your wardrobe. It really does make your life easier to have a single touchstone for color. You can add colorful touches or cool jewelry to spark it up.

4. There are blogs out there, find one whose style matches yours or that you aspire to. Don't be afraid to mimic outfits. One of my favorite outfits from last summer is a look I stole wholesale from Real Simple. Can't wait to bust it out this summer!

5. I like Real Simple and In Style for actual, wearable looks. Here's Real Simple's 10 Staples list.

6. Ask a stylish friend for help. People who like to shop, occassionally want to do it for other people. I know if a friend asked me, I'd be ALL over it! You are a living Barbie doll! I'd love to dress you!
posted by Ruthless Bunny at 11:52 AM on January 15, 2014

Response by poster: Followup info:

I don't really go many places other than work (trying to work on my social life though!). It's technically business casual and I do have some sort of business casual things I bought when I started there (all black, natch). It took about 2 weeks before I defaulted back to jeans/hoodie, and no one has ever said anything to me. Mostly because I just get to stay in my office all day, I imagine.

I suppose if I could dress similarly for work/going out that'd be useful. I am not so worried about work attire though.

As far as height, I am 5' 8", and slightly less than ideal weight for such height, so not super tall, but taller than average.
posted by polywomp at 11:56 AM on January 15, 2014 [1 favorite]

Best answer: The important thing is that you're comfortable in your clothes.

It sounds like you're okay wearing more or less the same thing every day, you just want to look a bit better / more grown up? It's fine to have a uniform. I dress pretty much like you, except I sub in a cardigan for hoodies and get rid of anything that has holes or excessive wear (or only wear it for manual labor). I wear a "piece of flair" most days - jewelry or an "indoor" scarf. As long as you only wear one patterned piece at a time, it's probably not too garish.

Nordstrom personal shopper sounds like it would be overkill for your style. Start with getting rid of your beat up clothes, then slowly buy stuff you like, ideally from slightly nicer stores than you're used to. Buy a piece at a time and see if you wear it. Thrifts are a good way to push your fashion comfort zone - I stick to nicer brands because cheap stuff looks like hell by the time it gets to goodwill.
posted by momus_window at 11:59 AM on January 15, 2014 [2 favorites]

excellent advice above

also I'm not sure if you still go like a goth influenced look but Haute Macabre has links to goth influenced style in photos sets of $x and less. You might find a piece or two that you can mix into a new wardrobe.

If you'd like to not spend so much in the long term, once you're comfortable finding a style you could check out the discount stores for similar styles / shapes. Like if you go to Nordstrom for personal shopping it will give you an idea about what they carry and you could check out Nordstrom rack for bargains.
posted by oneear at 12:01 PM on January 15, 2014 [1 favorite]

While you're figuring out your style, buy stuff from thrift stores. You won't feel bad about trashing a $3 blouse that just doesn't look right.
posted by desjardins at 12:05 PM on January 15, 2014 [2 favorites]

How would you feel about taking a trip to a major department store and committing to JUST TRYING THINGS ON.

I came in to recommend going to an appointment with a stylist at Nordstrom or a similarly nice department store, but even just this is great advice for you if you're not ready to make that step.

I'd also like to say that if you're doing this without a stylist's help, don't be afraid to ask the other people in the dressing room their opinions! Last time I was buying jeans, a voice from a few stalls away called out "is anyone else in here dressed? Could you please poke your head out and tell me if these jeans fit ok on my butt?" and I was just like, wow, that lady is a genius.
posted by phunniemee at 12:07 PM on January 15, 2014 [2 favorites]

Best answer: I'm somewhat in your same boat in terms of personal (lack of) style, disliking shopping, and not really knowing what I want to wear in general. I also primarily do freelance work from home so have no real incentive to look good on a daily basis. However, I had a realization the other day that I could up my style game significantly (to me, at least) by making just a couple of easy, incremental changes.

Here's what I currently wear (basically exactly what you currently wear albeit maybe one step up) and how I'm swapping:

1. dark-blue skinny Gap jeans: keeping these
2. various short- and long-sleeved Gap t-shirts: keeping these (for now)
3. various colors of Roots hoodies: swapping these out for long hooded cardigans
4. adding a scarf: these can be found cheap and everywhere
5. adidas sneakers: swapping these out for short and/or tall boots

Upgrading in stages is seeming way more manageable to me than going for a complete overhaul all at once.
posted by hapax_legomenon at 12:07 PM on January 15, 2014 [10 favorites]

I'm taking it slow with Stitch Fix - on a monthly delivery system. So, after filling out my taste profile, once a month a stylist ships me a box with 5 items in it, including cards that give ideas on how to wear each item. I try everything on and mail back what I don't want in a prepaid envelope. Then they just charge you for what you keep. I've done this once so far and it was pretty fun, actually. They sent me a funky pair of jeans, a bold silk blouse, two sweaters and a funky necklace. I kept the jeans and sent the rest back.

I don't like spending money on myself. I don't like shopping and trying things on in the bad-lighting dressing rooms. But once a month I can do.
posted by jillithd at 12:08 PM on January 15, 2014 [1 favorite]

I want to second momus_window because this advice is so good! The easiest way for you to transition a bit is to just translate your existing wardrobe into a slightly nicer version of itself.

Ratty hoodie -----> high-quality cardigan with good buttons and a nice color

t-shirt ----> just always make it a slightly fancier t-shirt

jeans ----> new jeans in a dark wash and a trendy/flattering cut

sneakers ----> flats or some kind of Saucony/Adidas/what have you trendy sneaker.

If you have pierced ears, grab some appealing earrings (whatever that means to you) super-cheap at an H&M or an Old Navy. If earrings aren't your thing, maybe look for a fun ring or a necklace or a scarf you can work into your outfit for a little shiny. (Seriously, Old Navy, H&M, Forever 21--miles and miles of cheap accessories you can burn through until you find what you love. Then when you find what you love, go to Nordstrom and buy the actual good-quality version of it.)
posted by like_a_friend at 12:10 PM on January 15, 2014 [3 favorites]

Target almost always has a great selection of lightweight sweaters/cardigans that are fantastic as a substitute for a more casual hoodie. Upgrading that, and perhaps throwing on a scarf or a chunky necklace will upgrade the overall uniform without being pricey.
posted by bizzyb at 12:12 PM on January 15, 2014 [1 favorite]

I'm roughly your age and for work I need to dress nicely but ready-for-action: so basically jeans and t-shirts, but business casual. My personal style is "neutral and plain." But I've got fashionista friends who think I do okay and refer to me as "having style," so...

I basically second SusanPG above. More "high end" basics will look more sophisticated and polished than Target shirts. Right now some of my favorites are Vince, Theory, and Everlane.

I thrift a lot (basically: natural fibers and/or new-looking high-end brands ONLY), and otherwise stalk the clearance rack and discount sites like ( is run by Amazon, and I've occasionally found jeans there for $30, so stalk it).
posted by jeweled accumulation at 12:12 PM on January 15, 2014

Yeah for work, substitute a cardigan for the hoodie and ballet flats for the sneakers, and bam! You're business casual. That said, you'll probably need to try some different cardigans on to find one that works. When you do, buy it in as many colors as look good on you (and you can afford). Ta da, you have a work uniform. You do not need to worry about what you're wearing to work.

As for "going out" it really depends on who you're going out with and how they're dressing. I guess also where you're going. But mostly who you're going with (like, you can go to the opera and some people will be dressed like they're going to prom and some will be in jeans and t-shirts - you don't want to be in a t-shirt when your companions are wearing cocktail dresses, OR VICE VERSA).
posted by mskyle at 12:13 PM on January 15, 2014 [2 favorites]

Who do you look like? Who do you want to look like?
posted by oceanjesse at 12:16 PM on January 15, 2014

Regarding what SusanPG said: if you are a former goth and liked that style I strongly suggest Allsaints Spitalfields. Many of the former-goths that I know adore their fashions, but they can only be worn by people who are tall and slender with narrow hips (which rules out 90% of the former goths I know).

Yes, it is expensive, but you can buy just a few anchor pieces and combine them with pieces from elsewhere. If you find outfits you like, you can also buy items that look similar to what they have, but elsewhere at a lower cost.
posted by rednikki at 12:17 PM on January 15, 2014 [3 favorites]

Get a full-length mirror, if you don't already have one. Being able to see your entire outfit on yourself is phenomenally useful.

Next, go through your closet and find your absolute favorite things. If you remember favorite clothes from the past that you no longer have, keep those in mind too. For each favorite piece of clothing, figure out what exactly you like: it could be the color, the softness of the fabric, the length, the neckline, the fit, etc. This is the very beginning of your personal what-to-wear formula. (For instance, I prefer scoop-neck tees and skirts that hit just above the knee, I never wear brown, and I avoid dry-clean-only anything. I figured these out through trial and error, and though I could find exceptions to these rules, it's easier for me to stick to them.)

Check out the Building A Remixable Wardrobe posts from Putting Me Together (via Nimmie Amee's collection of links) - it breaks things down into tops, bottoms, "completer pieces" (e.g. cardigans and jackets), and accessories. I tend to put together outfits using these four categories, and it helps me.

Experiment with venturing a little bit outside your comfort zone, but keep in mind that you're also free to ignore any style advice that isn't your taste. I used to avoid belts, tucking in shirts, and any styles that were fitted around the waist - and I still don't do them often, but I tried them all this year and actually looked kind of good! But you will never convince me to wear a belt over a cardigan, and I'm still not wearing brown.
posted by Metroid Baby at 12:26 PM on January 15, 2014 [3 favorites]

I shop at thrift stores in areas where wealthy people live and discard a lot of amazing, brand name clothing. I am no fashionista but my style is sort of preppy/outdoorsy and there is a ton of Gap/Banana Republic/LL Bean/Anne Taylor stuff being donated to thrift stores in my area, and I can pick it up for $5-$10 in like new condition. I too balk at the idea of paying full store prices for clothing - if I do shop at the mall, I shop the clearance racks. Clothing prices are ridiculous.

I find if I go into the thrift store looking for basic colors and basic items - like cardigans, blouses, khakis, jeans - I can usually find a few things that fit me pretty well and are high quality brands/fabrics.

Definitely get rid of anything unflattering and that you don't wear, and unless you truly love it, get rid of stained or ripped items, but don't donate the stained/ripped/with holes items to the thrift stores - it will just be a waste of their time sorting these items as they cannot be sold. Either cut them up into rags or throw them away.
posted by treehorn+bunny at 12:38 PM on January 15, 2014

There's another thing that works for me on my step 2 above (discarding unliked stuff). You can tell you don't like it because you have an instinctive sinking feeling when you see it. Maybe you suppress that feeling, but come on. Some other askme features a husband who saves stuff: that's me. Have a bag where you put the stuff you "really shouldn't" throw out. Put the unliked stuff in there for a trial period.

If you do have a trusted friend, take same to Goodwill, where s/he can prevent you from buying things like knits that are already a tiny bit worn, and help you find perfect new stuff (like this ankle-length A-line Laura Ashley khaki skirt on my person right now, cost $7.99).
posted by skbw at 12:42 PM on January 15, 2014 [1 favorite]

I am not someone who appreciates fashion. I can appreciate pretty things, but putting together a wardrobe and choosing outfits makes me break out in hives. This fact makes my grandmother break out in hives, so for college graduation she bought me a professional shopper.

So seriously, find a professional shopper. Not one at Nordstrom's, because yes, those people are just sales folks with great taste. Like with financial services, a flat fee independent professional shopper will put your needs first.

We bought fancy bras because it's "such an important foundation", but she dragged me to Target and DSW for items that were in line with what I could afford sans my grandmother's generosity.

If you don't have time for blogs, you don't have time flitting through a thrift store to find your look on a budget. You want to be doing other things. You don't need to learn fashion when the world is full of people who are a million times better and want to do it for you (even if they also want to pay rent, and need you to pay them).
posted by politikitty at 12:45 PM on January 15, 2014 [3 favorites]

I can't tell if something would or would not look good. If I try it on, maybe, but due to some longstanding body and self-image issues, my automatic expectation is that it'd make me feel awful, even though I know my overly critical view of myself is unrealistic and biased.

What does make you feel comfortable?

Can you make a list of actual clothes you've had that you really enjoyed wearing, and build from there?

Like, let's say you usually hate skirts, but at one point you had one you didn't mind so much. What was that skirt like? Is it possible to find more skirts that match that description?

Or lets say that you have one top you consistently get compliments on at work. Can you figure out what it is about that top, and then find more of the same?

To give an example from my own wardrobe, I have this one particular brown velvet blazer that I adore. It just feels right. I feel attractive and powerful and even pretty in it. Because of this, I've decided three things:

- If it matches my beloved brown velvet blazer, I will almost certainly buy it (so as to get more opportunities to wear said blazer).

- If I'm in the market for a nice work-appropriate light jacket, a slightly dressed down blazer is a great option.

- I have a feeling that I look better in dark brown than black.

Thus I took an item I actually do like and used that to find some direction for future new things. Rather than just wandering through H&M being overwhelmed and thinking everything would be awful.
posted by Sara C. at 12:48 PM on January 15, 2014 [1 favorite]

My sister in fashionlessness! I am slowly but surely getting better at this (people compliment me on things I'm wearing, sometimes, which has never happened before in my life.) My primary goal is to look like a normal professional masculine-side-of-lady person in her 30's and not the slouchy poor grunge kid I was in high school.

Secondhand stores helped me get over the hump. For some reason, ugly clothes don't make ME ugly when they're inexpensive. Plus, it's easier to try, say, 10 different red sweaters, each of a totally different style, and decide what does and doesn't work about each. It's different than a store that has decided that This Season's Style Is Ruffles and sorting through stuff that all looks bad in the same exact way.

I consciously decided on a uniform of sorts, which is: black/gray pants or black/gray skirt, plain fitted tops in anything-but-grayscale, and sometimes a scarf or shawl. I also own jeans, and most of the black-pants outfits go just fine with them. I decided on this by looking through my closet at the stuff that made me happiest and least happy. As I get more comfortable in knowing what I like, and as things wear out, I've been more comfortable with spending a little more money on good quality clothes, because I know I will like that sweater for the next 10 years.
posted by tchemgrrl at 12:50 PM on January 15, 2014 [2 favorites]

Go get your colours done with a friend. It's a bit of a lark, and relatively cheap for what you get: you find out exactly which colours make you look good, and which make you look washed out / dead. You also usually get your own personal colour wallet for reference.

It's a terrific way of narrowing down your focus when you go shopping — you can instantly dismiss all the unsuitable colours and head straight for the stuff that counts.

I'm struggling to find a link to a service near you, but I'm sure you can find one with a bit of digging.

Can't help with any of the other stuff, sorry. I'm a very happy jeans and t-shirt person.
posted by ZipRibbons at 12:52 PM on January 15, 2014 [1 favorite]

I am by no means a fashionista, but I think I kind of get it. With that said, on a whim, I started binge-watching, "What Not to Wear" on Netflix and learned a lot. Some things I was already doing, some not and some I was just learning how to fully put together an outfit! Perhaps watching a show like that could go into one of your first steps as well as they break-down how to pull together an outfit, what to look for and what not to.

For instance, you can do, solid+print+texture. In other words, a basic pant (black slacks or dark jeans), a cool top with a pattern, and then add a fitted tweed coat. Top it off with some cool shoes (on the show the women seem almost forced into getting heels more often than I think is necessary), and jewlery.
posted by wocka wocka wocka at 1:20 PM on January 15, 2014

Best answer: 1. Shave legs
2. Buy some skirts
3. Get some boots

I am telling you, skirts+boots = cuuuuuuuute!! It looks like you put a lot of effort into dressing, when all you did was roll out of bed and put a skirt on.
posted by St. Peepsburg at 1:21 PM on January 15, 2014 [9 favorites]

If I had to trash my entire closet for some reason and start over this is where I would start:

-1 or 2 pairs of super dark navy jeans
-A bunch of white shirts (button downs, tshirts, slightly dressier tees, turtlenecks)
-A bunch of black shirts (same types)
-1 pair black slacks
-1 pair gray or brown slacks
-1 black pencil skirt
-1 gray or brown pencil skirt
-1 black dress
-1 color or print dress
-a bunch of cardigans in various colors and weights
-Neutral color necessities (underwear, socks, tights)

If that were my entire closet stock, I could probably go into my closet blindfolded and still do pretty decently. Obviously YMMV depending on the look you want.

Re: clothes shopping price guilt, you can get basics like those above at a pretty decent cost from,, and goodwill. (Check their clearence and sales sections too.) You just need to be patient and not expect to buy everything at once. Building a wardrobe is a process and you should feel free to be meticulous in what you add.
posted by donut_princess at 1:25 PM on January 15, 2014 [1 favorite]

Also, re colors and the whole "get your colors done" idea:

Big secret, you don't actually need to pay someone to do this, nor do you need to buy a bunch of swatch books and the like.

It's all about the contrast between your various facial features (hair, skin, eyes, basically), as well as what kinds of undertones your skin has. There are a few tests online that have you do things like hold a white sheet of paper up to your face to see your skin's undertones, etc. and say what color your hair and eyes are, and then they tell you what your "season" is and show you a color palette and a bunch of celebrities that have similar coloring to yours.

From there, you can either just remember the color palette (mine is jewel tones, muted shades, and cooler colors, with navy, grey, and brown in lieu of black), or you can pick one or two celebrities and endlessly look at pictures of them and see what colors they wear. If that doesn't terrify you.
posted by Sara C. at 1:25 PM on January 15, 2014 [1 favorite]

Response by poster: I just wanted to say I think these answers have all been super helpful. I think I may have a little more confidence to try again, and maybe from a different approach, and incorporating some of these suggestions.

I'd bring a friend to help if I could, but I don't know anyone I could ask.
posted by polywomp at 1:48 PM on January 15, 2014

Go into Express, try on some stuff you like. I'm the same age as you and also have the teenager or soccer mom/old person dilemma. Express comes closest to my idealized "grown up" version of my former goth/raver self.

Also, for the cheap-o in me, I frequent Forever-21. They have all sorts of basically disposible clothing there that's cheap and cute--and a huge variety so you can find age-appropriate basics. For example, I bought my skinny jeans there for $20.

Spend a day trying stuff on. Get a feel for what you like.
posted by katypickle at 1:52 PM on January 15, 2014

Best answer: I hired a stylist for an online consultation recently to solve similar issues I was having, and it was totally worth the money. It was less expensive than hiring an in person consultant, and the process was absolutely fantastic. It was literally one of the 10 best things I've ever spent money on.
posted by OrangeDisk at 1:53 PM on January 15, 2014 [6 favorites]

Dressing is a skill you can learn systematically. You might find that a lot of things in your current wardrobe are just fine, if you combine them right. Follow me:

Measure your bust, the circumference of your shoulders, your waist, and your hips. That will give you an idea of relative proportions. It's late now so I can't get to the exact formulas, but it sounds like you kind of have a grasp on the horizontal proportions already. But if you are sufficiently motivated, MeMail me.

Measure the length of your head, from the top of your head to your chin. Now measure your full height. Divide your full height by your head length.

Measure your leg length from the soles of your feet to your crotch. Divide by your head length. If your legs are more than 4 head lengths long, you have long legs. If they are less than 4 head lengths long, you have short legs. Bang on 4 head lengths, and your legs are proportionate.

Measure your rise length, which is your natural waist down to your crotch. If your rise is more than 1 head length long, you have a long rise. Less, and you have a short rise. 1 head length and your rise is proportionate.

Measure from your natural waist to your chin. This is your waist length. A proportionate waist is 3 head lengths long. More, you are longwaisted, and less, you are shortwaisted.

Now, get a copy of Trinny & Susannah's "The Rules". Take a look at each body detail (big bust/no bust, etc.) Now look at your measurements to see whether a category applies to you. Try to take the emotion out of it and focus on the numbers. If you get stuck, MeMail me.

Supposing it turns out that you have a big bust. Take an item out of your closet. There are clothes that are recommended for busty women and clothes that are anti-recommended. Try to work out whether the garment you're looking at is recommended or anti-recommended. Remember, just focus on the bust for now. Over time, you will build up a complete picture.

Once you've decided whether that garment is supposed to look bad or good on you (shape-wise, you can move on to colour later), put it on and wear it for a day. If it's bad, well presumably you've been wearing it up to now, so you won't end up looking worse than you already have been. But, while you're wearing it, try to take in your observations about it and get a feel for why it's bad or why it's good. At the end of the day, write that garment down on a list, check a column Y/N as to its suitability, and make notes if you want to.

The next day, take out another garment and do the same. Do this for a few days, then move on to the next feature (like "no waist" or something).

People complain that this system is confusing because a style is recommended for one feature that they have, but anti-recommended for another feature that they have. The answer is that a garment that is "bad" in any category should be ruled out. What's left will be the good garments that fit both features.

After some time, you will have really taken in the idea of what shapes look good on you and what shapes don't, and you will have done this using your own wardrobe; you haven't bought anything yet.

Now let's consider colour. I have to say, I'm not nuts about all this colour-analysis business. Here's what you do. Take a pile of clothes and stand in good daylight. Hold a garment up to your chin. The garments that make you look younger and smoother and brighter are in good colours for you. The ones that make you look more crumpled and haggard are in bad colours for you. If something's in a bad colour, you can still wear it, but keep it away from your face - save that colour for skirts and pants, etc.

If, after a while, you are feeling hopelessly lumpy and as if nothing you can do is ever going to help, you are probably suffering from Bad Underwear. Bikini panties will give you quadributt; thongs will give you Cellulite On Parade. For example. If either of those things apply, shorts are recommended.

I realise this probably goes against your nature but if you really want to start building on the best foundations (har), you should see if you have a branch of Rigby & Peller anywhere within travelling distance and book a consultation with them. Their underwear is so expensive... but to be honest, from what you've said, I think you can afford it. And if you do this once... you will know into the future what underwear fits you best, and which styles to shop for at a much lower price point. Think about it.

And after you master that, we can move on to the really advanced stuff. Your adventure awaits you.
posted by tel3path at 2:42 PM on January 15, 2014 [11 favorites]

I second the YouLookFab and Already Pretty blogs/forums as good resources for "learning" about personal style. One place to start is identifying your body type--from your description, you sound like a ruler/rectangle, but here's how to tell:

1) Undress to your best-fitting bra and underwear (or leggings and a fitted tank if that makes you more comfortable) in front of a full-length mirror. Look at the visual horizontal width of the following places: shoulders, bust, waist, hips. Do you have strong shoulders or narrow, possibly sloping shoulders? Is your waist visibly smaller than your bust and/or hips, or is it almost undefined?

2) Take a cloth tape measure (or a piece of string, but I really recommend the tape measure--it will be useful in the future and isn't expensive to purchase) and measure the following places on your body: bust at the widest point, waist at the smallest point, hips and butt at the widest point.

3) Based on assessments from BOTH #1 and #2, think about which of the following body types is most similar to you (and you might well be a combination of two types):

a) Strong shoulders OR significant bustline paired with narrow hips = inverted triangle.

b) Wider hips, narrow waist, and small bust = pear. The low waist/hip ratio combined with high waist/bust ratio is a defining attribute of the pear shape.

c) Relatively similar bust/waist/hips from front visual (#1) = rectangle. For purposes of getting basic body-type-based fashion advice from the internet, if you have a curvy rear but narrow hipbones, it's better to define your bottom half by the hips (or by #1 visuals over #2 measurements).

d) Wider/undefined waist and medium to large bustline = apple.

Now, armed with body type information, you can narrow down your search for online resources--there are lots of webpages to tell you what "will" and "won't" work for a given body type. Don't take these rules as the absolute truth, but they're a good place to start if you have no idea.

You might also benefit from finding a few "uniforms" that work for you and repeating them. This is actually a technique that "fashionable" people use all the time, and it will help you feel put together once you hit upon a "formula" that you like.
posted by serelliya at 2:58 PM on January 15, 2014

Hi! I'm 33 and figuring this out this year too. :)

Seconding the advice to watch What Not To Wear. Check them out on Netflix.

Putting Me Together - Wardrobe From Scratch includes:
  • Part 1: Defining Your Style and Lifestyle Needs
  • Part 2: Choosing Wardrobe Colors
  • Part 3: Basic Guide to Proper Fit
  • Part 3b: Alterations and Tailoring 101
  • Part 4: The Starter Kit Shopping List
  • Part 5: Case Studies
You are going to relax so much when you learn the concept of a 'capsule' or 'remixable' wardrobe (related: 'uniforms'). With a remixable wardrobe, you have fewer clothes but you can mix and match them together easily — any permutation makes an outfit that works. Grab and go.

Putting Me Together - Building A Remixable Wardrobe includes:
  • Part 1: Reimagining Clothes
  • Part 2: Shopping for Remixable Pieces
  • Part 3: The Importance of Colored Bottoms
  • Part 4: Layering Pieces
  • Part 5: Accessorizing
I've built a Pinterest board of remixable wardrobes because I find this idea so helpful.

Already Pretty has been mentioned lots of times already because it is so awesome, and its stand-out characteristic is the way it deals with emotions around clothes and body image. Check out How To Dress Joyously for a taste of her approach. There are many more like this in her Body Musings section of the Greatest Hits page.
posted by heatherann at 3:21 PM on January 15, 2014 [6 favorites]

I'd describe my style similarly. I also only wear t shirts and jeans, although I do have nice winter shoes. I don't care about fashion, I don't own accessories or jewelry, etc. However six months ago I felt my appearance was lacking. None of jeans fit well, my t-shirts were getting shabby, etc. I do have some nice clothes because I would have liked to dress nicely, but in reality, I hate dressing up, especially for working at computer the entire day, so I never wear them.

What worked for me was to find a good source of quality t-shirts (fitted, heavy weight cotton). I bought three, made sure I was happy with them, then bought another four (at 30$/t shirt). I also bought new jeans that fit me better (I'm short and curvy, can't give you any recommendations), at around 80$, and bought another copy of the same pair later. So now I have two pairs of nice jeans, seven nice t-shirts. Instead of sweatshirts, I have black basic Icebreaker sweaters - sporty, but better than sweatshirts. I like the ones with the zip at the neck. I have two or three of them, and you can wash them in the washing machine every once in a while. So it's basically an upgraded t-shirt, jeans and sweatshirts look. Still comfy, requires no thought or effort in the morning, but looks much better than ill-fitting jeans and 10$ t-shirts. I have a couple of sweatshirt and a couple of other pants around for some variety if I really want it. You can add a leather belt if you're feeling fancy.

I buy relatively expensive t-shirts and jeans but the clothes last for years, and I can usually re-buy the same model a couple of years later so I don't have to go through the traumatic experience of looking for new clothes.

Edit: Wanted to add that in the past I tried to change my clothing style, but for me easy-care and comfort overrule wanting to look nice for work, esp. since my work does not require it.
posted by sockpuppetdirect at 4:52 PM on January 15, 2014

Also, number one thing I have done recently to upgrade my look and clothes confidence: lingerie fitting. I was wearing the wrong size bra and the right bra really changed how some garments fit on me. Some clothes that I had liked no longer fit well and others that had been ready to go in the discard bin have been rescued to become valuable members of my wardrobe! If you're doing a complete wardrobe refit, start with a good fitting--from a specialty store (NOT Victoria's Secret)--and be sure to wear the new bras when trying things on. It makes a huge difference, especially if you dress in T-shirts a lot, and I do.
posted by immlass at 5:00 PM on January 15, 2014

Best answer: I didn't know about Putting Me Together before this question, and I have to say that's one of the best resources for having A Grownup Wardrobe I've ever seen.

I really struggle with how much and what kinds of clothes to actually have, and her Building A Wardrobe From Scratch really clarifies things. I'm not building a wardrobe from scratch -- and if I had to guess I think you're probably not, either -- but it was super easy to see how to not just have all jeans, or how not to end up with a bunch of stuff that doesn't go together.

Protip: you will see A LOT of tips about ways to layer and accessorize and putting belts over cardigans and the like. What it all really boils down to is that you should always have a third item. Just t-shirt + jeans looks blah. T-shirt + jeans + cardigan looks fab! As does t-shirt + jeans + cute belt, or t-shirt + jeans + statement necklace, or really anything where there is a third item in play. You don't necessarily have to try the fashion bloggers' twee combos of scarves and belts and wearing a million layers. You just need to have that vital third item.
posted by Sara C. at 5:14 PM on January 15, 2014 [6 favorites]

Oh, and I'll also nth just making the stuff you already like slightly better.

Wear a $10 Target tee, boot cut light-wash jeans, a washed out grey hoodie with your college logo and a hole in it, and white running shoes?

Instead, get a $15 Gap tee, more stylish jeans in a dark wash, a cardigan, and a pair of supergas. You're now adorable!

Get a $20 Urban Outfitters tee, black skinny jeans, a blazer, and a pair of brothel creepers. You're now a serious trendsetter!

And yet, same basic look, and you're still definitely within the range of ordinary clothes you can afford on a middle class salary, not $300 dresses.
posted by Sara C. at 5:22 PM on January 15, 2014 [2 favorites]

Look at people you think look good, maybe take a picture with your phone, and try to replicate the look. Ignore fashion magazines and find bloggers who post pictures. Do try a cute skirt with your usual hoodie and tee. Or a cute top with your jeans. Wear your favorite jeans and try on lots of tops. Wear your favorite tee and try on skirts. Try on lots of stuff, make a few purchases and integrate new stuff into daily wear. Part of looking good is looking like you put in some effort. Also, buy good shoes, maybe a really cute pair of Keens, or something else cute and comfortable. Cute boots definitely elevate your look. You may have to spend on shoes and boots, but check for sales.

I try to buy tshirts at Talbots or Landsend on sale; better quality means they last longer and fit better. I find cute skirts at thrift shops.

Get properly-fitting nice underwear; it helps your clothes look better and gives you a confidence boost. Try on everything in your closet, and get rid of stuff that doesn't fit or is worn out. Mend, hem, repair, replace buttons on anything that needs it.

I pretty much choose 1 from column a (a skirt or pants I like) and 1 from column b (a cotton sweater or tee) and then add a jacket in cool weather, maybe cute tights if I chose solids, maybe a scarf. It took me a long time to feel comfortable and feel that I had my own style, and now I feel pretty good.
posted by theora55 at 6:07 PM on January 15, 2014

Semi-stylish (hopefully!) but low-maintenance young woman working in tech in SF here.

Overall tips: stick with solid colors in relative neutrals (grays, blacks, khaki/beige, brown, olive, navy, some red) and everything will mostly match. Pick simple patterns (stripes, dots) to start.

You are going to get a HUGE boost just by replacing the hoodies with cardigans and the sneakers with cute boots/flats, and throwing on one piece of jewelry everyday.

Here's my basic wardrobe. This is what I actually wear day-to-day, not including: fancy events for which I have a couple dresses, nice slacks, and blazers; beach trips; skiing; weekend athletic and lounging around clothes, etc. It sounds like we have a similar body types (tall and lanky). I don't like to worry too much about clothes, I like everything to be easy to mix and match.

Bottoms: I wear skinny or straight leg jeans pretty much everyday (I buy most of my denim from Levi's for <>

I also have a handful of skirts/dresses (which I wear with solid opaque black tights from Walgreen's and boots, so they are wintery skirts in heavier, darker fabrics not summer skirts) and a two pairs of stretchy legging-pants (heavy real fabric, not just cotton), which are little edgy at work and perfect for going out.

Tops: Easiest thing is pretty tanks and tees that can be layered. Stick with fabric that won't pill (silky, linen, etc. rather than the softer knits). Look at Ann Taylor, the Gap, Anthropologie, Banana Republic, thrift stores, Old Navy, J. Crew Ambiance on Haight, and small boutiques. Look for what you like - I do mostly solid colors or very simply classic patterns, I like scoop neck instead of v-neck, etc. They should not be too tight, but also not too loose (no gaping at the armpit). I also have a bunch of simple cotton t-shirts (long and short sleeved) in various colors, mostly from J. Crew but you can get them everywhere. You want the really thin "tissue" cotton to make it a little dressier. Start with black, gray, navy, olive green, etc. and add colors you like.

Layers: The cardigan is the grown-up hoodie. Pick up long-sleeve cardigans in black, beige, navy and gray and you can wear them over almost anything. Advanced level: soft unstructured blazers, "grandpa" sweaters.

Shoes: Two pairs of boots: tall (just under knee-height) black flat-heeled, brown (tall or ankle height, flat or low-heeled). You can also look for a third fun pair eventually. One pair black flats, 1-3 pairs colored flats (red, gray, brown, olive, leopard print). One pair medium-height simple black almond-toe pumps. Cute sneakers for dress-down Friday.

Accessories: A couple of pairs of earrings (fake pearl studs, sturdy small silver hoops), a couple bracelets (just go to the jewelry counter and pick one you like! <$25), a couple necklaces (again, just start with one you like). Don't stress about it; just put on one piece of jewelry a day. A few scarfs in solid colors (a linen fabric is nice in SF) or simple patterns - the kind you can wear inside all day, not for outside warmth). A cute backpack if you bike, or tote bag if you don't and prefer that.
posted by amaire at 6:19 PM on January 15, 2014 [4 favorites]

In addition, if you want some budget conscious fashion advice consider:
A fashion consultant named Leslie runs this service; you pay a fee, answer some questions, send in a couple of pictures and she will advise you about your color "season" and also what "figure type" you are...and give you advice on what types of clothing will flatter.

I have used this service and it has made a big difference in the clothes I buy and the colors I wear. You can also subscribe to a weekly outfit recommendation service for either 3 months or by the year. It is pretty cheap, considering, I think under $50 a year for the whole thing. She takes each body type every week, goes to a store (or a store's website) and sends out an email with pics of the different skirts, pants, shirts and accessories she recommends for each body type. Now that I have been subscribing for a few months, I have the best clothing styles for my shape downpat. fyi...I am not a paid employee, just a happy customer...
posted by bessiemae at 6:24 PM on January 15, 2014 [2 favorites]

Alternative perspective:

I hate trying a million things on.
I hate going into a store, trying to figure out if a shirt suits me, and if it doesn't, does the other near-identical style of shirt look better? How about in a different colour? How about in a different size?
I end up trying on 12 different shirts before figuring out I hate all of them. Well, by the end of it I hate them, anyway.

From that perspective, I find shopping in upmarket vintage stores easier. I look at the clothes. If I think I might like the item of clothing? I try it on. It either fits well, and I decide whether to get it, or it goes back on the shelf. No trauma except when something really lovely looking doesn't zip up at the back etc.
I find it much less of a mental strain. Yes or No, not 'No but maybe that variation instead?'

Additionally, fabrics tend to be better. If it was going to fall apart, it would have already, and I'm more able to wrap my head around it being worth the money, because even at the pricier vintage stores - this *is* pretty much the resale value.

I'm now 'better enough' at clothes, that I can buy new clothes.

Also, to contrast, some people find vintage stores far more overwhelming, so, it depends what makes an easy decision for you.

Dresses can be easier. I wasn't a dress person, but it was easier to see if it looked nice on me. It's a single piece of clothing, not a really matchy piece where I have to make multiple decisions, so getting a nice little black dress which is kind of worky, kind of casual, with boots, can take a lot of the effort out.
posted by Elysum at 7:00 PM on January 15, 2014 [1 favorite]

I have had similar problems, and actually did the Nordstrom's personal shopper thing, and then hired for cash money an actual personal shopper. The Nordstrom's shopper didn't work for me at all, and the hired personal shopper was ok, but it wasn't the greatest experience. I did get some useful tips and information, but I felt like she didn't really "get" me and thought I was kind of a sad sack.

We're the same height, and it can be a difficult area - "regular" can be a little too short, and "tall" is too long unless you wear mega-heels.

I also have body-image issues, and I find that often when I try stuff on I get in a cycle of: this looks bad > clothes don't fit my body > I feel like crap > I suck. I don't have the same body issues that you do, but I do have the kind of body other people claim to envy but can be much harder to dress than people realize. But you have to find a way to power through and try stuff on. Try try try. Sometimes I go in with the mindset that I'm going to try stuff on and it will all be terrible. And then something isn't terrible. Win!

I also come from a less-advantaged background, and I struggled with how much to spend on clothes. The thing is, pretty much everybody puts stuff on sale. I like Clarks shoes, which are generally around the $100 mark, but I wandered into a Clarks store when they were having a sale and got three pairs shoes for under $110 including a pair they mailed to my house for free because the store didn't have the color I wanted in my size. You can get much higher quality and service at nicer places for about the same or slightly higher than you would pay at Target. I have found this to be true again and again, and I continue to be amazed by it.

1. Shave legs
2. Buy some skirts
3. Get some boots
In the winter you can skip Step 1 by wearing tights, which is why I wear more skirts in the winter.

posted by jeoc at 7:07 PM on January 15, 2014 [1 favorite]

Long further answer because I'm enjoying this question :-) Here are some other things I do, that might be helpful for you too. (I am super-pragmatic about clothes: I like to look put together, but I want to put in minimum effort into getting there.)

* Like juliplease said upthread, pick one general colour scheme you like and don't buy anything that doesn't fit into it. For me it's white/grey/charcoal/black, but it could just as easily be 'earth tones plus sky blue' or 'desaturated primaries plus denim.' The point is that you want everything to be in the same family so you can mix it together every morning without thinking. You might worry other people find this boring but they don't: they are not actually paying very much attention :-)

* Figure out one or two silhouettes that look good on you and only buy the components that make up that silhouette. So for example mine are i) narrow trousers with a hip-length shirt and fitted short jacket, and ii) wide-legged trousers with a fitted crew-neck top and suit jacket with the sleeves pushed up. This makes it way easier to shop because I just buy the components of the silhouette I like, which means I can ignore everything else. (Like, I ignore 'dolman-sleeved tunic,' all forms of dresses and skirts, cropped or pleated anything, 'things that are oversized.' Yay.) Basically the purpose of this is to figure out what works once and then replicate it, rather than trying to design an outfit from scratch every single day.

* Stop buying categories you don't wear. I did this by hanging the stuff I'd worn, after cleaning it, on the left-hand side of the closet. Gradually the right-hand side of the closet became the domain of ignored things, and then I know to stop buying them. Like, I used to buy a lot of skirts, and eventually I realized I never wore them, so I stopped buying new ones. (This I think is a variant of the old shopping adage 'buy for the weight you are, not the weight you hope to be.')

* Pick one or two types of accessories and ignore all the others. So for example I don't wear bracelets or rings or necklaces or earrings or belts or hats, but I do wear scarves because I have a tendency to get cold, and I carry bags because I have a lot of stuff to drag around. So I pay a fair bit of attention to bags and scarves, and ignore everything else. If you focus on a small number of types of accessories, that streamlines your morning as well -- it becomes a question of 'which scarf, if any' rather than a super-open-ended question about how, in general, to adorn yourself and how it all fits together.

* If you can afford it, I'd say don't buy on sale. Honestly, there's a reason stuff is on sale: usually it's because it didn't sell :-) You will get a better return on investment, IME, by just sucking it up and paying full price. That's how you end up with stuff you will wear happily for years.

One last thing. The single simplest best step you could take to upgrade your style, I'm guessing, would be to ditch the hoodies in favour of something slightly more stylish. Try something like this or this or this -- any of those would probably make a big difference. Another easy step would be a pair of short boots to replace your sneakers, like maybe something like this or this.

Good luck! I think it would be fun to shop with you, but we're not in the same city: oh well :-)
posted by Susan PG at 8:06 PM on January 15, 2014 [1 favorite]

As someone who appreciates minimalist clothes, I regret that Eileen Fisher's silhouettes don't flatter me. I think they're meant more for someone with a build like yours.

As far as price points are concerned, something I think about is how often I will wear something, so I try to project a price per use. Objectively, it was ridiculous of me to spend $200 on a dress when I was in grad school, but I wore it once a week all summer for years, so my price per use was probably ultimately comparable to an inexpensive t-shirt and skirt, which wouldn't have lasted anywhere near as long, or looked as nice. (The tip about a skirt and boots applies to dresses, too. A comfortable dress is a wonderful thing because it reads as putting in more effort than it actually requires.) Something well-made that feels nice and that I like is worth spending more money on. Something that will merely do the job of making me suitably not naked is not.

Shoes and bags, in my opinion, depend more on your lifestyle. I rarely spend less than $125 on shoes because I walk about a mile to work and have finicky feet, and that's just where the market is for the kind of shoes I'm after. I would spend $300 on a classic, sturdy bag that met my needs and that I loved the look of -- I don't have a car, so my bags get used daily, and put through quite a bit of wear and tear.
posted by EvaDestruction at 10:09 PM on January 15, 2014 [1 favorite]

I would not shop at Eileen Fisher if you're under 40 and work in a "young" field. If you're an attorney or work in finance it could work, but that look will really age you if you work in any sort of tech or media context.

I think their clothes are lovely, but they're the sort of thing I'd like to wear someday.
posted by Sara C. at 10:23 PM on January 15, 2014 [2 favorites]

I went through a massive overhaul of my look a few years ago, and here's some of what helped me:

Nthing What Not to Wear. Just keep watching - Stacy & Clinton are fun and great at explaining their wardrobe strategy, and it's easy enough that it will sink in quickly. Also, it was super helpful to me to realize that I am DEFINITELY not the only woman in the world who has had trouble managing my look.

Of course, then you need to take that learning out of the living room and into the stores. I schedule a research field trip downtown, hitting everything from Target to Nordstrom, about once every 4-5 months. It's an all day adventure, and all I do on these days is try stuff on - I don't even bring my credit card with me.

Over time, this kind of research has taught me what cuts and patterns work best for me, so now when I do actual shopping, it goes much faster because I know exactly what I am looking for. I also learned which stores, and which labels at which stores, work best for me for particular items - I don't waste time anymore looking for shirts at Target or Old Navy, for example, since they rarely fit me right at those places.

I also generally stick to a limited palette - black, blue, purple, cream, and silver. Black is my favorite neutral; I usually use it for my pants/skirt rather than closer to my face because the wrong tone washes me out. I have blue eyes with a yellow/cream ring around the iris, so blue, purple and cream tops, jackets and scarves make my eyes look intense. Most of my jewelry is silver, like the highlights in my hair.

I found it really helpful to name what I was going for with my look - having a couple of adjectives in my head is also a great tool when shopping. Mine are artsy and urbane. So when I shop, I'm thinking, does this item bring the artsy or urbane to my look? If not, back on the rack you go, clothes. If the clothes aren't serving the purpose you set for them, you don't need them.
posted by deliciae at 10:49 PM on January 15, 2014

Just wanted to share these two blogs with you. Both ladies rock black designer outfits - everything is about the style and fit rather than the colour/pattern.
posted by Ness at 2:31 AM on January 16, 2014

Best answer: I just looked at your profile, then went to your web site - and was blown away by your fantasy art!

You actually know a lot about clothes and the human form, because you draw these things, and so beautifully!

You didn't say anything about wanting to become a living advertisment for your art - but why not break out some amazing clothes that tie in to what you create, perhaps initially just for special occasions - openings, client meetings, nights out, or anytime you're being celebrated?

In your profile/avatar pic, you looke like a da Vinci madonna. Go for this fantasy next time you dress up for an event. I love the slinky, flowing, super-romantic things the women in your illustrations wear. Try a strapless wine-colored dress sometime- doesn't have to be full-length, but it could be. Or just get used to baring your shoulders - tube tops with jeans and cute flats or other closed shoes. You can make this work for your office by adding a shrug, then you can take it off that night in a restaurant. Chandelier earrings would work amazingly well with your botticelli waves and delicate features. You're tall, so you can wear big earrings, anything really. Large earrings emphasize facial symmetry and would be great choice for you.

You have length - do you know how lucky you are! You have the perfect frame for almost any kind of garment. You can wear menswear coats, you can wear maxi skirts, you can wear big statement bags - try something with fabric and beads. Emphasize what characterizes you. Try platforms or comfy heels - you'll look even more statuesque.

Think in terms of your characteristic style. You're dressing in a utilitarian way right now, but your soul is romantic, and this is why you're seeking a change. Dress for your soul. Go for romance! Just apply some of your artistic imagination to your clothes. Your body is your canvas. Have fun with it!
posted by cartoonella at 5:28 AM on January 16, 2014 [5 favorites]

Re: friend, I one time bought a stylish acquaintance dinner in return for her help with a particular outfit (family anniversary). A friendly acquaintance, even if not a friend per se, might be flattered.
posted by skbw at 10:49 AM on January 16, 2014

Well with your figure and youth and former goth style, I don't really think you could go wrong with just upgrading your pieces you have now. One caveat would be on the hoodie front - I find a lot of hoodies allow too much space in the gut area, like i could steal a bunch of bananas and noone would notice type space. Look for something longer, leaner, more closely fitted to your skin. tailor it if you need too. if you wear all black or all neutrals then put on some lipstick or do your eyes to really pop (makeup counts, right? It's like clothes for your face i guess). make either the lips or eyes a statement, but with neutal colors. I'm a lipstick girl, I have a nice berry color that makes a statement, but not like FIRE ENGINE RED LIPS _ DARING TREND! statement. You could try that or a nice deep dusty rose, or some other complimentary color to your skin. Or you could focus on eyes and just use a neutral shimeryish shadow on your lid, mascara, and line your lower waterline with eyeliner. Advance 1 space by using a second slightly darker shadow color and blending just a little from the outer corner of your lid inwards. Pass go and collect $200 if you can handle that whole cat eyes liquid eyeliner thing.
posted by WeekendJen at 10:56 AM on January 16, 2014

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