Off The Cuff: Searching For Style When You're Not Loving Your Body

Wearing heels to the pool. As you do.

Wearing heels to the pool. As you do.

Dear Winona,

I’ve gained a lot of weight over the last year, and in that time my style has changed from “bright, fun, and flirty” to “dark, drab, and shapeless.” I want to wear cool clothes no matter what my body size, but I feel overwhelmed by the idea of shopping for a new wardrobe, especially when I’m uncomfortable with my body and mostly want to hide it right now. Help!


What’s My Style Again?

Dear WMSA,

This has happened to me so many times over the course of my life: I start feeling not great about my body for whatever reason, and buy shapeless, baggy clothes accordingly. Before I know it, I have a whole closet full of dark-colored sacks that make getting dressed in the morning a downright dreary affair. “Where’s the personality?” I ask my closet. “Where the fun? Where’s the ME?”

The best way to break this pattern is to learn to recognize it before it’s too late (and by “too late” here I mean the point when your closet looks like a storage area for the Supreme Court’s robe collection). When you’re out shopping, if you realize the main quality you’re looking for in your clothing is how well it allows you to hide or blend into the background, put down your credit card and give yourself a moment to reassess. It’s fine, to a point, to want to conceal or highlight certain physical features, and we all go through phases where we wish we could wear Harry Potter’s invisibility cloak and call it a day, but trust me on this: no one has ever bought a cheap, shapeless, baggy, black shirt and been like, “I’m SO glad I bought this.”

Maybe you want to downplay an area you’re feeling insecure about, maybe you’re not in the mood to wear eye-catching colors, but that doesn’t mean you have to buy clothes that effectively make you disappear completely. Don’t buy an item of clothing unless you can find some aspect of it — even something small — that makes you excited to wear it: a pretty drape, a color that brings out your eyes, a soft fabric that feels dreamy against your skin. There’s so much more to style than shape and size. Focus on those things.

This is really the thesis of my advice to you: let yourself rediscover the aspects of fashion that you used to be excited about. Find ways to get excited about them again.

Chances are your “bright, fun, and flirty” description of your personal style extended to so much more than the size and shape of your clothing. What did you love about the clothes you wore before? Beautiful colors? Gorgeous patterns? Did the fabric feel amazing on your skin? Were they created by a talented designer you admire? Were they unique finds from vintage stores you loved? Reconnect with some of the things you loved about clothes before, because guess what? None of these things hinge on a specific size.

Another piece of practical advice that I give all the time (because it’s just so useful!) is this: accessories, accessories, accessories. It’s daunting and expensive to try to overhaul your entire wardrobe at once. For a quick way to bring some much-needed flair and excitement to your look, treat yourself to a few fabulous accessories that feel bright and fun and YOU: necklaces, sunglasses, scarves, shoes. All of these small touches can make a big difference in your overall look, and help you try out different styles without spending a ton of money.

Because here’s the thing: a shapeless, baggy, black dress with no accessories is drab and sad. A shapeless, baggy, black dress with a huge, badass tiger necklace? Fierce. Undeniably fierce.

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