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.