How to I dress beyond the one-leg-in-the-pants-at-a-time?

July 9, 2013 4:21 AM

OK, so I need to dress better -- up my act, look a bit classier or cuter or generally not like a boy in college. Part eleventy billion.

Stats: 30 year old lady, 5'9, hovering routinely between 170 and 180, 36DD, hourglass shape. I'm working on bringing my overall weight down for good, but my body distributes weight quite evenly so my basic shape usually stays the same. I'm frequently taken for being in my early or middle 20s, which is a good thing for the most part.

Problem: Wardrobe is from the Target clearance rack, Goodwill or local consignment shops. Colors faded, fabric stretched, etc. I usually wear one of my two pairs of jeans (boot cut) and a t-shirtish top, although they're not baggy or shapeless, just sort of boring. I don't have a clear picture of what I want, but when I've thought about it *really* hard, I think the chicks in TV shows like Supernatural are sort of my (imaginary) style. Maybe.

Solution: Point me to blogs / websites / stores about how to dress better, flatter my body or skin, remembering to accessorize, etc., or tell me how you managed to take your appearance a step-up and where you draw inspiration. Things with pictures would obviously be great.

Bonus: leaving for the Caribbean on Saturday; if you can suggest items that would look great but still be practical at home, you get extra yays.

posted by mibo to Clothing, Beauty, & Fashion (10 answers total)

Oh, I am you! Or I was four years ago.

Here are the things I have learned since then that have helped. YMMV.

1. This lady (the blog author, not the person featured on the front page right now) has similar proportions to you. She has much wisdom and inspiration on the matter of dressing yourself.

2. You may now bag up all your hoodies and men's tshirts and put them in your attic.

3. If you have an hourglass shape, then it will look better treated as three thirds rather than two halves. So, if you put horizontal lines near your actual real waist, and/or somewhere below your hips, that will be more flattering than having a line across your hips, which is what most jeans/tshirt combos will do for you.

4. Many dresses and skirts will look awesome on you. Skirts that fall from your natural waist will be good, as will dresses that don't have a seam running across the waist area at all. Tunics will also probably look good with leggings or skinny jeans. You may need to get some boots and/or flats if you normally wear trainers - if your hips are pretty wide then boots may look better than flats.

5. Some fashion jargon that may help: Aline, fit and flare, princess seams.
posted by emilyw at 5:02 AM on July 9, 2013

Hi, I have your shape and I'm fat!

I think one thing that will help is to think of your style by way of an icon or something.

Glamourous movie star
Tom Boy
French Librarian (someone here has that one, but I think it's genius.)
Hot for Teacher

Personally, with your build, I'd go for Joan Holloway Harris, and rock the '60's retro thing.

Now, I'm short waisted, so that really puts a monkey wrench into things. Basically, I can't tuck my shirts in. So I layer them over things. This works really well. Today I'm wearing a long blue and white paisley skirt, with a navy top over it. I have a concha belt over that. So I'm accentuating my waist, but I don't look like my boobs are sitting on top of my thighs.

I will say this, get a well-fitting bra. You don't know what your real bra size is, so go to Nordstrom and get fitted. Then buy one great bra and rinse it out every night in the sink with the stuff they sell by the cash register. This is KEY if you have a large bosom. Hint, it will be a Wacoal and it will cost about $60.

I'm really loving Prep 101, I get it on my feed on Facebook and it gives you some ideas for outfits. Another source is InStyle magazine. Every month they show you what the trends are, and then give you ideas for how to add them to your wardrobe.

One look I'm totally rocking right now is a navy striped skirt, they showed a horizontal pencil, with a teal tank and a denim shirt with the sleeves rolled up. Very cute and easy to wear. With my curves, I got a long, A-line, with strategic stripes. I wear it with an orange tank and a short sleeved, denim jacket. I have orange sandals and a leather handbag. I am well put together but it's as comfy as my PJs.

I find that I get amazing deals at Macy's. Their Women's department has a ton of stuff to choose from. Their sales are great, and if you use their card, you get a 15% discount most days. If you're there a lot, you get coupons in the mail. Also there's always a coupon in the newspaper, so 20% off is normal. Combine with a sale or the clearance rack and you're buying things for under $10 if you catch them on a good day.

Some of the best advice I ever got was: Don't buy it unless it's 100% perfect. If it's uncomfortable, boxy, itchy, a bad color or ill-fitting, even if it's free, it's no bargain.
posted by Ruthless Bunny at 5:59 AM on July 9, 2013

When I rebuilt my wardrobe (mostly from thrift/consignment/garage sale finds BTW) I drew heavily from The Vivienne Files for inspiration. She tends towards monochromatic outfits with coordinating scarves and jewelry, or wardrobes with only a few neutral colors as bases. I prefer more colors than this, but seeing the building blocks was extraordinarily helpful to me when putting together my shopping list.

She also posts a lot about packing for trips, including a recent post on packing light for a warm-weather vacation. Again, you don't have to like these items or color scheme, it's just a way to visualize what sort of pieces you might want to bring with.

I am really a big fan of finding secondhand bargains and then spending the rest of my clothing budget on tailoring. Particularly since you have an hourglass shape, you will probably have to get boxier pieces like blazers and shift dresses taken in at the waist.
posted by payoto at 8:21 AM on July 9, 2013

Sometimes the easiest thing is to evolve your wardrobe, rather than making a radical change all at once. Usually wear t-shirts? Maybe get one that's a bit more fitted, or a bit more decorative, or in some way more luxurious or grown-up than you're used to. See whether wearing it makes you feel fab and like a spiffier, updated version of yourself. If so, look further in that direction.

Similarly, if you tend to wear shapeless skirts, try getting one of the fun new retro ones with flare and color, see what you can do with it, what kind of shirt at the same store seems to go with it and feel good to you. If that works, bingo! try another! If you can't make yourself wear it, then maybe try updating your pants instead, adding a pair of cargoes or a different shape of jeans.

Baby steps. Once you get a bit bolder, try a department store, and find a friendly salesperson to bring you some scarves or necklaces that pop with the clothes you're trying on. Even if you don't buy anything, you'll have started to grow your notion of what is possible, your vocabulary of what's out there. Every time you get a combination that really feels great, you'll have your own motivation to remember to put it together when you want the extra zip in your setp...

good luck! try to have some fun with the explorations, rather than just piling up some self-recriminations for not having done so sooner. it's never too late to expand your options!
posted by acm at 9:45 AM on July 9, 2013

I would recommend going into a big department store like Nordstroms or Bloomingdale's that carries many brands and just try on lots of things in all the brands in your price range. Especially bottoms - trousers, jeans, skirts, whichever suits you and feels comfortable and looks right in the mirror. Try them with the kinds of tops you feel comfortable wearing and see how they pair up. It's all about proportion. I find it much easier to find clothes now that I know there are certain labels and styles that always fit me well and others that are never cut right. For instance, I don't look good in A-lines despite the usual advice that they suit everyone, I'm 5'10" and the cut makes me look like I am wide with stick legs; pencil skirts are better, but I wouldn't have figured this out if I hadn't tried on dozens.

I think a few good, basic pairs of trousers/jeans/skirts that go with many things (ie navy, black, grey, neutrals) and fit you very well are the foundations to start with. Try on a lot and buy only what fits properly and feels right to you. It might be worth spending a little more on perfectly fitting basic jeans/trousers that you can wear several times a week.
posted by citron at 9:59 AM on July 9, 2013

About the bra - this is what a well-fitted 36DD looks like. I'm guessing this doesn't look like your bra.

If you are near a Nordstroms, get fitted there. If you don't have access to one, don't go to Victoria's Secret or La Senza or another department store. Get a cloth measuring tape, measure yourself, and go from there. Here is a collection of resources to help with that, and figuring out bras in general.

In a proper bra, clothes fit better. If you have back pain, the new bra will help.

If you figure this out soon, you can also get a bathing suit in your new bra size for your trip. Having something that fit me properly and held things in and up made me much more comfortable in a bathing suit.

Good luck!
posted by delezzo at 10:48 AM on July 9, 2013

When you go shopping, wear a bra that fits properly. Use this post to learn more. And wear nice panties, and clothes that you can take off and put back on easily - it makes trying stuff on so much easier. Go to a large store like Macys, and buy 1 new outfit. Probably a pair of great-fitting black pants, and a top that you love. When you try on pants, use the 3 way mirror and make sure you like the way they look from the back. To build your wardrobe, shop a lot for a while, to get used to trying on clothes and finding what suits you.

For a trip to the Caribbean, I'd pack 2 pr. shorts, 2 skirts, 4-5 tops that pretty much go with everything, 2 pair sandals, 2 bathing suits, 1 sarong (very large rayon square) that could also be used as a shawl/scarf, a couple of scarves.

Stuff I'd pack, based on my current wardrobe
shorts - khaki & navy
skirts - 1 cargo skirt(olive drab), 1 print skirt
tops - navy, olive drab & black girl tshirts, 1 black & white linen top, 1 white sleeveless linen top.
cargo skirt goes w/ all tops, print skirt goes w/ black & white tops, khaki shorts go w/ all tops, navy shorts go w/ all tops. If I wear navy shorts & navy tee, I wear a scarf, in summer, usually a bandana that isn't a typical bandana print. The sarong is for wrapping up in on the way to and from the beach. If I go out and want to feel more dressed up, print skirt and prettier sandals.

In my case, 75% of my clothes come from Goodwill. I shop fairly often, so I can find nice clothes that fit well. For your trip, you probably can't count on that. I buy the best footwear I can afford, because my feet are hard to fit (arthritis).
posted by theora55 at 12:03 PM on July 9, 2013

So from a quick google search it looks like the women in supernatural share general outfit ideas. Their most photographed outfits appear to consist of:

-A neutral colored t-shirt or a feminine blouse in white, black, or jewel tones
-A fitted jacket in brown leather, black leather, plum, a canvas-y neutral, or a canvas-y green
-Fitted dark pants.

The open jacket serves a few purposes. It adds depth to the look, fitted leather adds structure to the outfit and by remaining open it gives a further illusion of vertical height to the torso.

You could easily recreate some of this look with the places you go clothes shopping. Goodwill can be a great place to find unique feminine tops and classic fitted leather jackets. I would try Walmart or Target for affordable dark pants. Just remember to think about whether a piece would actually fit that "look" when you take it off the rack. Definitely look for inspiration in the feminine tops shown above. A top with textural details makes a huge difference when you are keeping everything else simple, and will still look great in the summer when you can't wear a jacket all the time.

The women in Supernatural appear to wear minimal jewelry. Many of them keep their hair long. Makeup looks like a particular focus on the eyes with some blush. The brows are all groomed.

Good luck!
posted by donut_princess at 3:28 PM on July 9, 2013

This may not be helpful to you, but I've found that how I dress, and my inspiration/enthusiasm to dress and style myself a certain way is largely dependent upon music/art/movies. If you are a music/movie lover, use them as your muse. The sound, the time period they evoke, the artists themselves. In the past year, I've integrated certain elements/accessories/trends inspired purely by the musical soundscape of my life to the point where I, and others, consider them my trademarks.

I never feel inspired to put together an outfit just for the sake of it, but if I am listening to a song or watching a movie that is reminiscent of something else, of a lifestyle, of some grander aesthetic of being alive, then it's worth it to me to present myself in a certain way. Because it isn't just a Tuesday in a cute outfit, it's me channeling something greater than myself and in turn, making that same cute outfit into something more.
posted by 2X2LcallingCQ at 9:00 PM on July 9, 2013

I came back to address your Caribbean Trip.

Go get a bunch of pretty tropical dresses. Buy some Pettipants or Spanx to wear under them. Not to smoosh yourself into the dresses, but to keep your thighs from rubbing together.

You won't be sad, and you'll be comfortable.
posted by Ruthless Bunny at 9:38 AM on July 10, 2013