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How to Totally Own Ugly Chic

There was a time when I'd be a little intimidated by the girl at the party wearing the Rick Owens leather jacket, the Helmut Lang dress, the pointy-toe ankle boots. But now it's usually the chick in the ripped NBA t-shirt, Marni flatforms and slightly greasy hair (in a good way) that gets me. I don't know when the backlash started, but somehow, ugly chic started to trump brooding polish in coolness factor. It's the nonchalance that nails it.

Still, ugly chic—or derelict, or crazy hipster grandma, whatever you want to call it—isn't the absolute easiest look to pull off. Those so-bad-they're-good things (Kenzo's '70s carpet sweaters, Prada's Eastern artifact sandals) would look seriously weird as the only statement accent in a plain jeans/basic t-shirt/preppy handbag ensemble. Instead, they need pairings that echo their kitschiness so the look reads intentional. And yeah, intimidating, and awesome.

Add wedge sneakers and a varsity jacket.

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