What can I do to become more girly and overcome my jeans/t-shirt/converse comfort zone?
October 17, 2007 1:43 PM   Subscribe

I get really depressed imagining the rest of my life being spent wearing jeans/shirts and my hair pulled back in a ponytail, so I need your help

I own fashion magazines, I love looking at fashion, clothes, I like shopping, makeup, etc. But when I try anything on myself it looks like crap and I buy a pair of jeans instead.

I don't have any female friends that I would feel very comfortable sharing makeup tips and having dress up parties with. I don't mind trying anything new but I just never think it works for me.

What do you suggest I do?
posted by icarus to Clothing, Beauty, & Fashion (27 answers total) 39 users marked this as a favorite
 
Your profile doesn't say where you are, but hit your largest department store and use their personal shopper service. Whenever I've used them I've ended up buying something that I would never have picked up off the rack and it ended up looking pretty damn good.
posted by meerkatty at 1:45 PM on October 17, 2007


Try using a personal shopper. Stores like Macy's or Nordstroms offer the service for free.

Also, I'm wondering if they look like crap because the they don't fit? The other option is find something you like and then get take it to a tailor and get it fitter for your body. This is especially good if you can find the item you like at a deep discount (like Nordstrom's Rack).
posted by metahawk at 1:47 PM on October 17, 2007


Response by poster: Forgot to mention that I'm in my early 20s and not 16. Which, I think, makes this even more depressing.
posted by icarus at 1:48 PM on October 17, 2007


Start watching What Not to Wear. While their catty "repartee" can get old quickly and they don't always make the best choices, they do impart some solid advice to the guests/victims.
posted by Pollomacho at 1:51 PM on October 17, 2007


I am a guy. When I had the same problem, I went to a store whose clothes liked and said to the salesman "I look bad. Make me look better. I will spend $X." and I left with clothes that got me compliments. I should wear them more, I guess.
posted by procrastination at 1:51 PM on October 17, 2007


Do you have any sisters or a mom to go shopping with you? My mom and my sisters are all brutally honest so I will ask their opinion about clothes if I am not 100% certain.

Or do you have any guy friends who would come with you?

As others have mentioned, higher-end department stores have personal shopping services. I have never used them myself, though I have been tempted many times.

And What Not to Wear is a great resource. I personally prefer the advice of the British WNTW women over the American version but both are very good at identifying what types of clothing look good on what types of bodies.

Also, I have had great luck going to the Bobbi Brown counter at my local Bloomingdales and saying, "I am clueless about makeup, help me." I feel very confident in my makeup skills now.
posted by sutel at 1:57 PM on October 17, 2007


Find a good seamstress. (Bonus points if she works from home.) Having your clothes made to fit your body and your aesthetic is, in many cases, actually cheaper than buying off the rack. And even if you end up paying more for an item than you would at Macy's or Target, the piece will be made for you and it will be unique.

You can usually find seamstresses by word of mouth so just start asking your friends where they get their clothes altered.

My mom makes dresses for a living (well she's semi-retred now). She's been known to recreate a dress from looking at an image from paused VCR tape. If you line in South Florida, I can help you track someone down.
posted by oddman at 2:02 PM on October 17, 2007


Nthing the personal shopper suggestions. Especially since most department stores offer the service for free. When I worked for Macy's I had no problem whatsoever accompanying someone around the store and suggesting pieces to wear.

Something I once suggested: Take a look at your furniture. What's your favorite place to lounge when you're at home? Your sofa? A favorite chair? Got tons of throw pillows you love snuggling with? Incorporate that color palette into your wardrobe.
posted by gummi at 2:06 PM on October 17, 2007


Best answer: Nthing What Not to Wear. One thing that I think is really good about the show is that you see how often people cling to what they're comfortable in, even though it looks bad or ridiculous. Hopefully watching it will make you a little more fearless. It's just clothes! They're fun!

Lately, I've been giving myself a set amount of cash to spend on clothes, and this has changed my buying habits. I used to buy whatever I could get for as little money as possible, which lead me to buy a lot of crap that looked bad that I quickly tossed. Now that I know I have a budgeted amount, I'm willing to spend a little more on something that really looks nice, which I think is going to pay off in the long term. I was scared of overspending before, so now that I have a set budget, I can be free within the limits I've set for myself.

As for the ponytail trap, cutting your hair too short for a ponytail would fix that problem. Always worked for me!
posted by ThePinkSuperhero at 2:06 PM on October 17, 2007 [2 favorites]


There is simply no way that you look bad in everything. One major big thing that I learned from watching the makeover / throw out your frumpy ass clothes shows on cable is that you have to start with your underwear. If your bra doesn't fit properly that is going to mess up the look of everything else you put on top of it. So I would start there.

Another thing is shoes. When you're trying on something nice - a dress, skirt, nice suit, whatever - you can't be trying them out in whatever sandals or tennis shoes you have on your feet when you're wearing jeans. It will throw off everything: how you stand in the clothes, how you carry yourself when you walk. I mean, of course a gorgeous dress looks kinda wierd and bad when you're standing in a fitting room in your stocking feet, but that's not how you are going to wear it, right? So, that's another biggie, having the right shoes on when you're fitting clothes.

Shopping assistance is also a big plus, and some of the better department stores actually make their employees develop clientele, so if you work up a rapport with a salesperson you could really benefit, since they have a real vested interest in helping you to be happy.
posted by contessa at 2:11 PM on October 17, 2007


Best answer: Hellooo me! I got some advice a while back that helped me:
- Improve your shoes. On days when I put on my clogs or sneakers, the rest of my outfit follows. So I bought some funky and functional shoes and now when I have them on, even jeans and a t-shirt seem to go up a notch. I don't think you have to be dressy, just have an opinion. So even clogs like this would convey more style. Also, if you hate heels, look into a low wedge. It's the only shoe with height that I feel comfortable with, but instantly makes me feel styled.

- Take the plunge with shirts. Look for shirts and blouses with some cleavage. Doesn't have to be a lot, and the shirt doesn't have to be expensive, but nothing says 'I'm a girl' like cleavage. It took me a couple of months to find my comfort level--literally--but now that I have I really think it looks a lot better than t-shirts do.

- Don't fight the ponytail. But do dress it up. I bought some nice barrettes and ponytail bands and this helps pull my look together from the top. Here's an example (I didn't buy my stuff there, but it looks like it has quite a range of styles). Etsy.com is great for this kind of thing, too. Here's a page of etsy ponytail holders.

- Find a couple of skirts that you know you'll wear. It's a skirt you want to wear out of the dressing room that minute. I have three that go a long way: a black rayon straight skirt from Banana Republic, a jeans skirt, and a cords skirt. All still very casual, but more feminine. Plus, add some interesting tights or leggings, some boots and a you look like this!
posted by cocoagirl at 2:18 PM on October 17, 2007 [1 favorite]


I agree totally with contessa re the underwear. I got fitted for a bra at Rigby & Peller (the Queen's corsetières, I believe) a week ago and it's been a revelation to me how much better my clothes fit with a bra the right size.

As for the rest of your question - I have spent the last umpteen years in jeans, so am no help at all but am interested in the answers.
posted by essexjan at 2:22 PM on October 17, 2007


Clothes that are in style never look good on everybody, not even the clothes that are known as something "anyone can wear". Different body types are flattered by different cuts of clothing, and different colorations are flattered by different colors of clothing. You need to find what flatters you.

Keep trying on things until you find something you like. This can take a while to find something that fits well and is flattering. Personally, I find it to be an annoying process, but you need to keep at it if you want to find a new style.

Shopping with female friends is highly overrated as far as helping you find clothing that looks good. It's more of a social outing.

As to the converse and t-shirts, you might take some small steps for a new casual look with some more fitted knit tops. Find some funky new casual shoes on zappos. These will be easier changes than suddenly moving to dresses and heels.
posted by yohko at 2:27 PM on October 17, 2007


please excuse the pop psychology but the most common theme on what not to wear is that most people were not comfortable owning who they were. Are you dressing like a 16year old because you don't feel grown-up enough to dress like a polished, competant, attractive 26 year old?
posted by metahawk at 2:35 PM on October 17, 2007 [1 favorite]


When I was a teenager, I wore what was comfortable, which was not usually particularly stylish. As I went into college, I went shopping with friends (not a dress-up party, just shopping, one friend at a time). I let them suggest things that I would normally never consider, and tried them on. I found a lot of cute new styles that way.
posted by IndigoRain at 2:42 PM on October 17, 2007


Response by poster: @Metahawk -- I don't feel like I look any more grown up when I try dressing my age. I can put on a dress or wear pants with a nice top/cardigan but I don't feel like I look any better.

I have very little female influence/inspiration in my life. I'm an only child and I was never very close to my mother, never had an overwhelming amount of female friends growing up.

I want to feel equally comfortable wearing "crap" and wearing nice clothes and I want to be able to switch between the two styles "effortlessly". Currently, I feel like I'm wearing "crap" regardless of what I put on.
posted by icarus at 2:49 PM on October 17, 2007


I own a shop where we teach sewing, knitting and other skills, so I'm up close and personal with the garment-fitting and patternmaking crowd. I absolutely, 1000% agree with the "start with the bra" approach. It's just huge. Really. A good bra should, and generally does, cost about $50 USD. And I'm talking good bra, not Victoria's Secret overpriced piece of crap.

Look for an old-school shop or department store where they are going to actively feel you up to make sure you're fitting into the bra properly.

(Gosh, how many times in a week do you get to recommend being felt up by old ladies in order to improve your looks?)

Nthing British version of What Not to Wear. Don't believe me on the feeling up thing? Sheesh, Susannah on WNTW feels up EVERYONE.

Nthing shoes. Zappos.com is a great alternative to dragging yourself to a million shoe stores, especially if you have big feet like me. You can search by color, style, you name it. If you're like me and enjoy comfy comfy, grab some Fluevogs -- funky yet comfy, and better-made than Steve Maddens. They inevitably look great with jeans, too. If you get the Mary Janes-y style Dansko clogs or the like, they can look very cute with a dress or skirt.

Are you crafty? Something like this is supercute, super-easy to make and will dress up any of your t-shirts. Hit up a really good quilting fabric store and you'll find some amazing fabrics. Bonus: no one else will have the same thing, and they're cheap & easy to make if you can sew even a little bit. Check the trim section of the fabric store and stitch some onto your t-shirt sleeves to dress them up!

Just a few ideas... good luck!
posted by bitter-girl.com at 2:55 PM on October 17, 2007 [1 favorite]


The Pocket Stylist has a great emphasis on what's good for particular body types and proportions. Understanding what's flattering (and not flattering) for your body type is the key to achieving the right "silhouette" for all your clothes, whether casual or dressy or professional. Then take a look at the Lucky Shopping Manual -- a very useful piece-by-piece guide for building a basic wardrobe, with subsections applicable to climate, type of profession, etc. And perhaps check out Tim Gunn's new book as well -- it's not so much a specific shopping guide as it is a way to consider the questions of who you are and how you want to present yourself.

Between those three books, I've learned more about how to dress well than I ever learned from 25 years of reading fashion mags.
posted by scody at 3:02 PM on October 17, 2007 [2 favorites]


Best answer: I'm a guy. One contrasting aspect (of many) of two of the women I've been in LTRs with is how they dress. Both of these women are good looking, but one would generally be content with clothes that fit "close enough." The other is really punctilious about finding clothes that fit "just so"--even when just shopping for jeans.

This makes shopping with the latter much more of a chore, but I have to admit, the difference is obvious, even to me. So, another vote for finding clothes that fit.

The former, to her great credit, would wear outfits that many other women would consider bordering on Halloween costumes. She got nothing but compliments on that, often from women who would say "I wish I could wear that." Her unspoken rejoinder was "you can." I have no idea if this is you, but if you've been holding back wearing something because you've got a notion stuck in your head "I can't wear that," just remember it's only in your head.
posted by adamrice at 3:03 PM on October 17, 2007 [3 favorites]


Best answer: Be a copy cat in real life, not magazines: Look at the people in the grocery store, at work, the mall, wherever you hang out. When you see somebody who looks the way you want to look, take a photo with your phone if possible, or make notes. Then try to recreate that look with 1 outfit. If there's a woman at work whose look you like, pay attention and try to copy some of it. Not iabsurdly, of course, but 2 women can buy gray tweedy slacks, a bright cotton sweater, and a scarf and look quite different.

Shop your closet: Try on the clothes you own in front of a good mirror with good lighting. Anything that doesn't look good on you, doesn't fit well, and is not in good repair should go right to charity, where it may look better on someone else. Fewer great clothes will look better than plentiful crummy clothes.

Wear the nicest shoes possible, and keep them repaired & shined. It makes a big difference.

Ponytail is fine if you have a good cut and you keep it clean and shiny, and use a nice barrette.
posted by theora55 at 3:31 PM on October 17, 2007 [1 favorite]


Best answer: Even just wearing corduroys that are cut like jeans, and a shirt with a bit of neck shaping (either v-neck, scoop neck, button-up, etc -- just something other than crew neck) can give you a more "defined" look. Doesn't have to be femme-y or alien-feeling, and it will probably make you look better, more adult. Baby steps at first.

Real leather shoes (with a low 1.5" heel and a boxy toe) were a revelation to me; you don't have to go for the super-high pointy-toe shoes to get real women's shoes.

Do watch What Not to Wear. Try to focus on the informative aspects and ignore the fluff, if you hate fluff. The two best pieces of all-purpose advice from What Not to Wear are: (1) only wear things that actually fit; get them tailored if they don't fit; and (2) try on things that are outside your normal comfort zone, because they really might surprise you once they're on.


I swear there was a great thread on here last winter about this question, but now I'm not finding it. So here are a few related...
alternatives to blue jeans (small steps)
some concrete tips (big steps)
good basics
about shoes
posted by LobsterMitten at 3:32 PM on October 17, 2007


Response by poster: You guys all kick some serious ass. I really appreciate all of the comments and suggestions you've made. Time for some closet-cleaning.
posted by icarus at 3:41 PM on October 17, 2007


My 2 cents here: beware the salesperson that constantly tells you that you look good in everything, especially if you are suspicious that it isn't all that great.

A good salesperson (in my opinion) will tell you what to look for (i.e. "this is in style now" or "these pants need to be fitted this way"), or will even tell you if you are better off shopping somewhere else (i.e. I am a smaller built guy, and some stores only sell things for wider or more built men).

Understand and accept your body type. I might want to look like Sylvester Stallone (or whoever is popular these days...) but if I have a body type like Brad Pitt, I can still look good, but only wearing the clothes that suit the same body type.

Clothes shopping is a skill. It can be long, frustrating and depressing when you begin, but once you learn the techniques, the shortcuts and the skills, it becomes easier.

Good luck!
posted by bitteroldman at 4:59 PM on October 17, 2007


I have one related bit of advice: Don't do a full 180 in terms of your wardrobe. Don't suddenly wear only dressier clothes, or buy a whole new set of clothing that's entirely unlike what you have now. It's probably better to upgrade your look in stages, like a nicer top with your regular jeans, or ballet flats instead of sneakers.

Maybe you'd be fine completely changing how you dress, but I tried that and failed. I, too, am a jeans-and-t-shirt sort of girl (and in my late 20s). A year ago I started buying and wearing more skirts and dresses and blazers, mostly because my boyfriend at the time nagged me into dressing that way. We broke up (thankfully) and now that I don't have anyone forcing me to dress up, I find that wearing that stuff now makes me feel like I'm "not me". So I reverted to jeans and t-shirts, and the only stuff I wear from that period are the blouses.

I'm just saying this in case you might find you've wasted money on things you really don't want to wear.
posted by sinderile at 5:07 PM on October 17, 2007


Jeans can look awesome, and quite polished if you choose the right ones and accessorize them properly. Some nice dark close fitting jeans with a pair of heels and a blazer is pretty much my winter uniform, and I feel dressed up and well put together, and comfortable as well.
posted by Sar at 6:20 PM on October 17, 2007


I recently came to the same conclusion and found this book really helpful (local library): Carol Spenser's Syle Directions for Women. Apparently there's a website too.
posted by b33j at 5:44 AM on October 18, 2007


if you try on one piece that looks good try on another of similar quality and a cut that goes with it, maybe? if you have on a t shirt a lot of nice pants/skirts might indeed look like crap, but they wouldn't if you wore a nice fitting sweater or top instead.

What Not to Wear is great. one thing i like about Stacey's style is, her skirts are just the right length. if a skirt is just a few inches too long and hits the thick part of your calves it looks dowdy and hemming it just a few inches shorter can make it totally stylish. oh, and wearing the right shoes too, a pointier toe is good with wider leg trousers or jeans.
posted by citron at 10:13 PM on October 18, 2007 [1 favorite]


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