Off The Cuff: What To Do When You Hate All Your Clothes

Dear Winona,

I don’t have a specific fashion question for you because my problem is harder to define. I’m feeling “bleh.” I just don’t like any of my clothes right now. I feel old and frumpy and out of style (and I’m only 32!) but I don’t have the money to buy a whole new wardrobe. How do I fix this?


Dear Kelly,

Alas, that vague, nebulous, soul-sucking trap of frump. It can strike suddenly and unexpectedly. You’re standing in front of a full closet muttering, “Ugh, I hate all of this.” You’re looking in the mirror thinking, “Ugh, I don’t like what I see.” You’re at work or happy hour or a party and feeling uncomfortable and awkward in your outfit and wanting to alternatively go on a shopping spree or hide in a dark corner. Unfortunately it’s a phase we all go through. Luckily, you don’t have to buy a whole new wardrobe to fix it. In fact, I’ve found that trying to cure frumpiness with aimless, frantic shopping sprees often actually makes things much worse.

I’ve written about how to cure frumpiness before, and how it’s often more of an emotional/life issue than it is a clothing one. For me, frumpiness usually hits when I’m in a major rut in my life, and I focus my frustration/unhappiness on my wardrobe because it’s more convenient than analyzing deeper issues. Be sure to open yourself up to the possibility that your feelings of “bleh” have to do with more than just your closet. But for the sake of this column, let’s focus on the fashion side of things. Because obviously an uninspiring closet isn’t helping the situation.

Shake Up Your Shopping Habits

Most us get a general idea of what clothes look good on us, and then gravitate toward those items again and again, for years and years and years. No matter the season, the current trends, our current body shape, or the evolution of our personal taste, we walk into a store and go straight for, say, the black fit-and-flare dresses, or the ponte pencil skirts, or the bootcut jeans, effectively wearing blinders that block out everything else. It’s great to learn what works for you and to shop efficiently, but this is also an easy way to get sucked into a frumpy rut, especially if your tastes and/or your body has changed but your shopping habits haven’t.

Make the conscious decision to shake things up next time you hit the mall. Try on items you’d never usually consider or don’t think you’re “allowed” to wear (like a crop top? Hell yes!). Stray as far away from your usual color palette and silhouettes as you can. Give yourself permission to try on things that will probably look weird or not great (and repeat after me: when clothes don’t fit it’s not your body’s fault!). Maybe everything will look kind of ridiculous, but maybe you’ll hit on a new style/silhouette/color that feels fresh and exciting. You don’t even have to buy anything, as long as you consciously branch out and remind yourself that there are other clothing options out there, and you’re not as limited in your style as you might feel right now. That right there is a powerful thing to remember.

Pick A Signature Accessory

Another way to break out of a style rut without breaking the bank? Pick a signature accessory that makes you feel fabulous. For me, it’s sunglasses. I can be wearing a dumpy black t-shirt and jeans that give me muffin top, but if I slip on a pair of glamorous, oversized sunglasses, I instantly feel stylish and badass. For you, it might be statement necklaces or a pile of colorful bracelets or some truly fabulous shoes. It’s entirely possible to redefine your style without buying a single new item of clothing. Invest in one fabulous accessory, or a few accessories in the same category (say, sparkly chandelier earrings or retro headbands) instead.

Your “accessory” could even be a particular style of manicure or lip color or hairstyle. Hone in on some part of your overall look -- besides your clothing -- that you’d like to focus a bit of time, energy, and money on, and it will pay off. You’ll look better, you’ll feel better, and who knows -- it might help guide your new style direction when you have a bit of extra cash to use on your wardrobe.

Host A Clothing Swap

At the risk of sounding like an anti-drug PSA from the ‘80s… Talk to your friends about frumpiness. Chances are some of them are struggling with the same feelings you are. And guess what? You guys can help each other through it without spending a dime. What’s that old adage? One woman’s frumpy maxi is another woman’s new favorite dress. Gather a group of friends together for a clothing swap. Have everyone bring a bag of clothes and accessories that they’re tired of and ready to part with. Make mimosas (this step is crucial) and then get to swapping. Not only will you all end up with some new-to-you clothes, free of charge, but you’ll enjoy the extra benefit of trying on clothes in front of a group of supportive friends. Sometimes, the best cure for frumpiness is a group of girlfriends gathered around you saying, “Oh my god you are KILLING IT in those pants!” Soak up those compliments. Because they’re totally right.

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