How to Lose a Guy in 10 Looks

Presumably since the dawn of time, there have been clothes that women love and men hate with an equal passion. Perhaps in the 19th century, it was the bonnet; in Roman times, maybe it was a loose fitting toga. Most recently, it’s been a high-waisted pant and statement fedoras.

The seemingly common thread? Trend-depending, of course, women tend to prefer to wear non-form-fitting clothing that often verges on quirky or unique—the clothing equivalent to “Jolie laide”—while men would rather we dress more like a Kardashian, nixing all superfluous ruffles, bagginess, and fuss.

Celebrated man-repellers throughout the years include Diane Keaton, Chloë Sevigny, Parker Posey, and of course, professional Man Repeller Leandra Medine, who’s forged an entire career off wearing the pieces that cause conflict amidst the gender divide. Note that all are fashion icons, appearing in numerous major campaigns and sitting high on the pop culture pedestal.

So this Valentine’s Day (and every day!), it’s up to you to decide who you want to please with your clothes: Yourself, or your dude? We’ll leave that one up to you! After all, there are so many ways to make your guy happy—but wearing any of these 10 items probably isn’t one of them.

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