There's a fine line between a risk-taking red carpet look that works — and one that's a worst dressed contender. Toeing that line takes the right combination of daring, flair, and next-level styling finesse to pull off. In other words, making a kooky outfit work ain't easy. But, without fashion risks, these bright-lights events would devolve into a bunch of pretty ladies in designer dresses — and where's the fun in that?
So, we're paying tribute to 16 celebrities who got the risk-to-reward ratio right and actually owned their offbeat outfits. Ahead, proof that fashion favors the bold.
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Miroslava Duma's solution for a ho-hum chambray-and-skinny-jean outfit? Throw a big ol' fashion blanket over it. Done.
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Vogue.com's Chioma Nnadi proves that any outfit, no matter how fancy, is instantly freshened up by a pair of unpretentious white kicks.
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We're not sure if Lauren Hutton is over heels, channeling John Lennon, or just taking the stuffing out of an ivory dinner suit with her slightly grubby white sneaks, but we do know we like it.
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All hail Jenna Lyons, queen of the quirkified basic. Her denim jacket? Ruffly and peplum-hemmed. Her white T-shirt? A tad longer than most. Her chinos? Ever so slightly drop-crotch. She is the patron saint of maximal minimalism.
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The shredded knit on Natalie Joos of Tales of Endearment makes us wish we hadn't tossed that top the Grumpy Cat in our life destroyed.
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We're used to seeing Kenzo prints as part of a fancy-pants ensemble, but artist and director Vashtie Kola took hers all the way downtown with her black Timbs and gold jewelry for a new spin on the girly matching set.
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As founder of Avenue32, Roberta Benteler has a literal store full of luxe designer goods at her fingertips. What charms us so much about this look is the winsome way she styles it — the '40s housewife headscarf, the cropped, wide-legged pant — so it looks retro-charming, and not just chi-chi.
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There are a few fine examples of the lady suit represented here, but Tao Okamoto makes hers next-level by wearing a shape even most dudes are afraid to tackle: the double-breasted jacket. Proof positive that you don't have to be this guy to rock one.