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The 50 Most Stylish New Yorkers Right Now Photo 1: grungygentleman.com; Photo 2 & 3: William Yan

27. Sean Sullivan

Occupation: Photographer/Curator, The Impossible Cool

Who would have thought a guy could build a personal brand from posting black-and-white photos of old white dudes? Well, mostly white dudes. Sean Sullivan's "The Impossible Cool" tumblr is a great source of inspiration for timeless style, which Sullivan exhibits himself. Often outfitted in simple, well-fitting garments, Sullivan seems to be grooming himself to be as classically handsome as the men whose photos he posts.

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