I'd pay like a million dollars for a simple pair of black shoes

July 6, 2009 10:22 AM

I'm 27 and feel like I dress like a teenager. How can I update my look whilst retaining quirkiness and personality?

Background: I'm in the UK, I work in a casual office. My old job - also casual - had quite a scruffy intake, but now I've moved into advertising I'm surrounded by People Who Make An Effort and I'm beginning to feel like the dowdy kid sister. Usually I wear jeans, a T-shirt and trainers to work, with the odd bit of kitsch jewellery...I started carrying a handbag a few years ago and I still can't think of it as a 'handbag' as surely this is what grown-ups have?

I'm tall and quite curvy, which rules out a lot of the clothes in the shops from time to time (I'm talking waaay too much cleavage, or things fitting everywhere but around the bust) which is very frustrating, particularly when shopping for vintage, and which makes em glad I don't work somewhere that involves suiting. I also have issue with heels as I have UKsize9 feet that are pretty tender. But I'm starting to feel unkempt and like I've let myself go a bit. I suffer with bipolar disorder and I'm trying to think of ways to help with the depression, and the shallow truth is that when I look pretty, I feel a bit better.

I don't want to go out and buy many new clothes - I have too many clothes as it is. I plan to get a haircut (I only get it cut once every so often - it's straight and flat and allergic to styling products) and, longer-term, lose a little weight. I have new glasses (Rayban tortoise-shell frames) which - call me sad if you like - makes me even more inclined to shift the rest of my appearance. I wear make-up, and try and experiment with new things so I don't wear the same stuff I did at sixteen, yet my wardrobe is stuck in my early twenties. I don't want to be a clone of the people I see around me or in meetings, and I don't want to simply take what the high-street is pushing this year. I want to still look like me, just a more put-together, more grown-up me. And I'm not sure of the ethics or usefulness of getting rid of half my stuff in order to find a coherent style. Any experiences or advice?

posted by mippy to clothing, beauty, & fashion (27 comments total)

I would start with cute flats instead of trainers. You don't need heels to look grown up--nice flats can really up the grown up factor of a t-shirt and jeans combination. Then you can add a cardigan or jacket and you've got a perfectly acceptable grown-up casual look.

This is assuming that the t-shirts are plain t-shirts and don't have graphic prints or logos or band names or funny sayings on them--if they do, switch to plain t-shirts with varying necklines and then add flats and a jacket.
posted by peanut_mcgillicuty at 10:32 AM on July 6

When I needed to look pro-casual, I usually went with pinstripe pants and sweater-vests over button-downs. Still easy, still mix-and-match, goes well with kitsch jewelry and funky glasses, and can still be worn with trainers if you so desire, or flats. Made me feel more dressy, with minimal effort/expense.

Also, even just making the switch from jeans to actual pants, while retaining al other clothing an daccessories, always went a long way toward making me feel more grown-up.
posted by esmerelda_jenkins at 10:33 AM on July 6

I'm not sure of the ethics or usefulness of getting rid of half my stuff in order to find a coherent style.

I can't speak to the "ethics" (is there such a thing as ethics for the closet?), but I think it's incredibly useful to get rid of old crap. Getting rid of the bad stuff makes room (physically and emotionally) for nicer things. We just did this for a friend last night- she's moving out of the country and needs to pare down a wardrobe that included stuff she's had since high school. Do you have people you trust who could come over and look at stuff with you? It was a big help to her to be able to try everything on in front of a panel of trustworthy friends, who were able to say stuff like, "Wow, that suit your Mom bought you in high school is so classic and gorgeous, love it!" and "Oh honey, that see-through lacy top is skanky, not sexy".
posted by ThePinkSuperhero at 10:37 AM on July 6 [1 favorite]

If you give your stuff away you should have no ethical qualms about it. Just make sure you're not doing it during a manic/hypomanic mood swing.

As a fellow busty and tall lady, I would suggest finding a few great plain shirts that fit and make you feel awesome. They should work with a lot of different outfits. If you get something that's a little baggy in the waist, you can sometimes get it taken in.

I would make sure you have a lot of tshirts or tanks that you feel comfortable in that can add a little fun to your wardrobe. H&M has a lot of cheap stuff that you can layer to change things up.

Jackets can actually really flatter your figure, again, you just need to find one or two that fit well and it'll make a world of difference in how you feel. I know you think it's impossible to find them for your dimensions but it's not, I promise.

Switch out the trainers for either really stylish ones (I long for sequined converse) or switch to flats or shoes with a small heel. Small heels can actually be a bit more comfortable than flats. Again, take the time to find a few pairs that are really great.
posted by kathrineg at 10:44 AM on July 6

No idea of your budget, but in the States many upmarket department stores offer what's called "personal shopping", in which you can be assisted sorting through the oceans of available clothing while you chat to the salesperson, who gives you second opinions and generally helps you out. Here's a testimonial from a mom, who, while she may not be exactly in your demographic, seemed really pleased with the service and assistance she got. Employees in these types of stores usually really know the lines, and they help hundreds of people a year find things, so it's not like they haven't seen someone asking similar questions before.

You also need not buy £500 worth of stuff; just tell them what you told us here - that you want to remain "you" at work, but not go from dressing like a 20-year-old to polyester twin sets. Have them bring you half a dozen outfits if you want, or just one; tell them your budget; try them on, chat to the person about what would work for you best. I don't know much about UK department stores, but it looks like John Lewis offers something like this. It's free, but you'd need to ring them up and book a time.

Good luck!
posted by mdonley at 10:57 AM on July 6

When you do get rid of stuff give it to charity, then you'll feel even better about getting rid of it. I agree with PinkSuperhero that friends are helpful.

Do you have any friends who are around the same shape as you? If so have a clothing exchange, everyone bring whatever they haven't worn in a while and share. The leftovers go to charity.
posted by mareli at 10:57 AM on July 6 [1 favorite]

Buy/find high-quality basic, neutral pieces and then show your quirky side with accessories: jewelry, bags, scarves, graphic tees under a more structured jacket, maybe a color streak in your hair?
posted by heather-b at 10:58 AM on July 6

You sound sort of ashamed for wanting to look better, and you've got to let that go. You seem to feel like any attention to style is somehow shallow and petty, but it's not, and even if it were, we all should get a little credit to be shallow in some aspect of our lives! The face you present to the world, which includes your clothes and general appearance, will affect how people respond to you, and I think an attention to that signals maturity and perspective. Taking pride in your appearance is something to be proud of, not ashamed of.
posted by you're a kitty! at 11:08 AM on July 6 [6 favorites]

I work in an ad agency!

Get rid of the trainers. Never ever wear trainers to work. Get some nice ballet flats for summer, and some flat boots or leather shoes for winter. Wear jeans that fit you properly. Get rid of tshirts that have anything 'promotional' printed on them, and only wear other tshirts as a layer under a vest or jacket or cardigan, or on their own if they are particularly stylish or fit you particularly well. Buy stuff that 'layers: button up shirts, vests, casual 'funky' blazers/jackets. Occasionally, wear a casual dress or skirt, and put whatever the heck you want with it.

If you want something short and sweet and easy to remember, a good short cut is:
1) Don't wear trainers/athletic shoes to work.
2) Don't wear t-shirts.
3) Wear any other kind of shoe or any kind of top, and you will look more professional grown up.
posted by Kololo at 11:11 AM on July 6 [1 favorite]

I always recommend "What Not to Wear." Here's the UK version, and here's the US version.
posted by decathecting at 11:15 AM on July 6

I second the cardigan recommendation. If you want to keep the t-shirt and jeans aesthetic (I do this), look for "fancy t-shirts"--that is, shirts that are essentially a cotton jersey material but that have been styled in a way that deviates from a standard tee (think gathering and unique necklines and subtle adornments). I've found that H&M is great for this sort of thing.
posted by penchant at 11:24 AM on July 6 [2 favorites]

You're lucky that in the UK there are a lot of cheap High Street shops that can outfit you well.

1. Get 1 or 2 pairs of well fitting dark jeans.
2. Get some ballet flats and ditch the trainers.
3. Get some cute tops - they're as comfortable as t-shirts, but dressier. French Connection, H&M, Monsoon, Oasis, etc. are swimming in these sort of tops. Try them on and if they fit decently, get it. Sure, they may fall apart after 6 washings, but they were cheap.
4. Get some cardigans at above mentioned stores when it is colder.
5. Once you get comfortable at these sort of stores, start browsing in the trousers. There are comfortable trousers that you can trade out for your jeans for dressier occasions.
posted by k8t at 11:28 AM on July 6

6. Get a few blazers as well as cardigans to spruce up your look.

And just dump your old clothes off at a charity shop... really.
posted by k8t at 11:29 AM on July 6

Go to vintage, thrift, and consignment stores for unique accessories: jewelery, scarves, and bags. My coolest accessories are from these stores, and I just use them with plain tops.
posted by jgirl at 11:36 AM on July 6

Work on accessories rather than trying to replace your entire wardrobe. Get cheap trendy accessories to modernize your look: scarves, a long necklace that can be looped, a fabulous bag, flats. It's all been said upthread, but Stacey and Clinton on What Not to Wear (U.S.) always recommend a fitted blazer, a pointy shoes, and dark wash jeans. Look for knit tees (not cotton), a couple of button-downs that fit, and a pair of black pants that can be casual or can be dressed up for things that you can wear to work and in your regular life. Also if you're busty, you might want to look into a bra fitting (even just at M&S or a proper lingerie store). So many women don't know what bra size they actually are and I think everyone should know what their size is -- it can change your life.
posted by pised at 11:57 AM on July 6

If you're anything like me, you probably get into the shopping version of writer's block (aka Shopping Block)-- you get stuck looking at the same styles you currently wear because you can't imagine yourself in the other stuff.

1) Bring a friend. They can see you in the other stuff objectively.

2) Don't wear your hair down or in a ponytail. For me, this means half ponytail, a headband or a braid. Maybe you have more skill with a blowdryer?

3) If it fits and isn't ugly, you should probably just buy it. Then, once you've got stacks of stuff at home, go through it all again and determine which pieces you don't need. It's easier to see what works and what doesn't when there's less pressure on each individual piece-- and less pressure on you as the Busy Consumer in the Busy Store. Return items as necessary. You'll keep a lot more of the items than you thought you would... and guess what? You'll wear them later, too.

4) It's hard to bargain shop when you're trying to change your style. Spend a day or two (or at least 3-5 hours) shopping in the non-sale section to get a better idea of what's working for you. THEN move over to the sale/outlet sections.
posted by samthemander at 12:41 PM on July 6 [1 favorite]

And I'm not sure of the ethics or usefulness of getting rid of half my stuff in order to find a coherent style.

Once you've figured out your new style - something I can't help with, since I'm struggling through that same issue myself! - do a ruthless paring down of your closet and donate your unwanted stuff. Perfectly ethical, and when all you have in your closet are things you love, it makes getting dressed so much easier.

Another bit of advice that a friend gave me, that I have found helps: buy less, buy the best you can afford, and buy only what you love.

As for shoes, well - among others, I love Camper shoes with my jeans and t-shirts when I want to wear something a little fancier than sneakers (or in my case, my usual clogs).
posted by chez shoes at 12:45 PM on July 6 [1 favorite]

My uncle is 50 and dresses like a teenager.
Then again, my uncle really is cool enough to pull it off. He just didn't change much from his jeans&T-shirt-days, so it's the natural way for him to dress.

I don't know how helpful that information will be to you, but I think it's relevant. Growing old is no reason to start listening to old LPs instead of CDs.
posted by Ingenting at 1:34 PM on July 6

Are you allergic to all hair products? There are a lot of products out there now that aren't full of chemicals, like natural beeswax pomades and stuff. If your hair is flat, a short haircut may make it look more interesting and keep it from looking stringy, or at least that's been my own experience.
You've gotten a lot of good tips on clothing, but just in general, don't feel bad about giving away old clothes. I used to have way too many clothes, all thrift store finds. many with small holes, stains, ill-fitting, etc. I gave away most of them to Goodwill and bought far less clothes to replace them. If you buy the right staples, you won't need a closet exploding with clothes to put together good outfits. What Not to Wear, as linked above, is a great show. I actually hear that the US version is better than the original UK version (for once) because the hosts are more real, but I've never seen the UK one myself.
posted by ishotjr at 2:33 PM on July 6

I second the Camper shoes recommendation and getting rid of clothes that are not making you look/feel great.
A nice blazer/coat makes an outfit look more put together. Since you're curvy, make sure the blazer/coat hits you at the hip/mid hip area and doesn't cover your bottom. I, too, would stick to A line skirts and dark wash, straight leg jeans as mentioned above. They are basic pieces to a working wardrobe. Remember to have jeans hemmed different lengths so you can wear some with heels and others with flats. If I find a pair of jeans I like, I get 2 pairs and have them hemmed differently. Also, I like wedge heels or platforms when I need to step it up at work but still have to be on my feet all day.
Try lots of stuff on, figure out what colors look good on you, and feel good about doing something nice for yourself. You are worth the time, effort and cost. remember that.
posted by bookshelves at 2:49 PM on July 6

I would suggest a personal shopper at Debenhams. They are not the world's most thrilling department store but they are a nice safe step from trainer, jeans and t-shirts to flats, jeans and not-t-shirts.
posted by DarlingBri at 4:42 PM on July 6

Non-shopping advice: Dress the way that will give you the least amount of trouble/most ability to gain, professionally. As a kid, I used to dress in quirky styles that showed off my personality. In some ways, though, I was relying on my clothes to show off my personality, at the expense of preventing me from fitting in with working environments. My advice would be to dress (at work, at least) in the standard work-style clothes. Let your personality be the thing that people notice, and choose to like you over, rather than that t-shirt you think was really witty.
posted by Ghidorah at 6:35 PM on July 6 [1 favorite]

I’m sorry this is stressing you out! Doesn’t it seem unfair that we should have to puzzle over clothes, for heaven’s sake? Couple of thoughts.

A shirt with a collar usually looks more put-together than one without. Of collarless shirts, square-necked ones look the sharpest.

When you have some time to observe people on the street, notice ones who look the way you would like to look and what they’re wearing.
posted by lakeroon at 9:40 PM on July 6

Thanks for the advice so far. Some points:

- Shirts will not fit me - I'm a size 16 with a 36FF bust, so would have to go to somewhere like Bravissimo to get a specially tailored one.

- I wear Converse-type trainers rather than gym shoes, but agree that flats are a good idea. It;s just hard to find anythign to fit my big feet! I used to own some Campers but they fell apart really quickly.

- I find it very hard to find trousers to fit - I have a wee pot belly, which stays there even when I've been at my most thin.

- I like Gok's Fashion Fix, because he emphasises how to alter outfits with customization, which I like because I can't make my own clothes (yet).
posted by mippy at 3:14 AM on July 7

I recommend Styleshake for designing your own clothes, but not having to actually make them yourself. I bought a pencil skirt and a mini-dress from them recently and I was impressed by how good the quality and the fit were, especially because you can specify your measurements really specifically - it's not just an off-the-peg size. And it's actually quite reasonably priced - about the same (or slightly less sometimes) as places like Oasis. I like my clothes to be super-simple (no ruffles etc), and this made it quite easy to get quite a grown-up look.
posted by featherboa at 4:08 AM on July 7

Consider skirts with control garments (like spanxs) , they can look super hot on a curvy lady. Pants are harder to fit.

I am the exaxt same size as you (woo boobie twins) and it is so, so worth it to get shirts made. Make sure you have the right undergarments too. I know how much of a pain in the ass it is. I know how everything tends to be a tent or a button-popping mess. It's worth it to feel good about yourself.
posted by kathrineg at 5:23 AM on July 7

So go to Bravissimo - chances are you'll need to invest in a proper bra anyway and they do coats, which are probably also a problem. It would be worth spending money on a nice well fitting shirt as you will feel great wearing it.

In terms of economical options consider stylish knitwear - it stretches to cover your boobs.
And is very affordable in all the supermarkets (I get most of my work wardrobe in Tesco) as well as the high street. Match with a nice t-shirt/vest top and some nice shoes and accessories and you'll look much more pulled together and grown up.

If you struggle to work out what styles and cuts flatter your shape I'd suggest Gok's virtual style consultation
posted by koahiatamadl at 11:01 AM on July 7