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7 Fashion Mistakes You'll Regret Forever

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By Connie Wang

Ask anyone: There’s nothing like a rule to make us want to break the rules. We’re clothing contrarians through and through, and proving that we can flip a “don’t” into a “do” is one of our great joys of getting dressed in the morning. And, if you’re the type to consider phrases like “No white after Labor Day” and “Don’t mix black and blue” as jokes and not helpful styling tips, you know what we’re talking about. Any guideline that makes you feel like you can do less with your clothes instead of more is one that deserves an #unfollow.

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That said, there are still some ways of dressing that truly feel antithetical to our whole philosophy on fashion. Clothes should make you feel more empowered, more beautiful, more sophisticated, and more free — not sloppy, bland, weak, or (and, yes, this happens) racist. Anything that does is almost, well, evil. So, we rounded up the style tips you should never take — think of these as the seven deadly sins of fashion. And, avoid them at any cost.

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Pairing skinny heels with short hemlines.

Don’t get us wrong — it’s not about baring too much skin or, heaven forbid, “slut shaming” — that’s not even in our vernacular. With a short hemline and a skinny heel, there’s a balance that’s not achieved much in the same way that coupling a combat boot and parachute pants or wearing sunglasses, earrings, a necklace, and lip gloss can feel lopsided. The solution? A high-waisted, wide-legged pant will make your legs look even longer (especially with a thin stiletto), or a miniskirt and a stacked heel with a mini platform will give you that vertical boost you’re looking for with just a fraction of the toe cramps.

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Wearing one designer head to toe.

Even if that designer is Zara or H&M, wearing only one genre, trend, or season makes you look like a walking advertisement, even if there’s no logo to be seen. Style is all about understanding clothing in and out of context, so it’s important to develop your mix-and-matching chops on the daily. (It doesn’t hurt that it’s fun to do, too.)

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Wearing clothes that almost fit (but obviously don’t).

Oversized clothes are meant to be oversized — same goes for shrunken. But, when your jeans are just an inch too pinched, your blazer hits you at the wrong place in the shoulders, or your heels almost fit (but you still have to shuffle around in them), you can feel awkward in your outfit. And, that’s never a good look.

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Sporting stains, hair, and grime.

We argue that a bit of lived-in-ness makes clothes feel more special. When your denim jacket has that perfect fray, or a button-up is slouchy in that cozy way, or your black jeans are your off-black jeans — those are the hallmarks of some much-loved items. But, if you’ve been a little lax on that love and your clothing is covered in grime, coffee stains, and your own hair, you aren’t properly taking care of your wardrobe. Not only will your clothes last longer with some TLC, but you’ll want to wear them more often, too.

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Appropriating from cultures in the name of fashion.

There’s a reason why feathered headdresses, Ganesh carvings, and Dutch wax cloth are so aesthetically compelling. There are whole cultures, religions, and groups of people to whom those images really speak, so wearing a symbol as powerful as those simply because you think it’s “cute” is reductive, to say the least.

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Wearing shoes and clothes that don’t let you move.

Too-tight dresses that won’t allow you to walk up steps in a straight line, razor-sharp boots that dice up your ankles each time you wear them, awkwardly “nice” bags that you have to be so precious with…if your clothes hinder your life, they’re not worth it. No one wants to sit on the sidelines, even for the sake of a pretty outfit.

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Pretending to be something you’re not.

Figuring out what you want to say with your clothes comes via a process of experimentation and boundary pushing. But, your clothes should always feel like an amplified version of you, even if you’re going for something different. If you feel like you’re playing dress-up, clothes become a costume, and that’s never a good thing. Who cares if none of your friends wear dresses, or if your dates never compliment your boyfriend jeans — if you don’t feel 100% authentic, don’t bother to please anyone else.

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