6. Josh Peskowitz

Occupation: Men's Fashion Director, Bloomingdales

Show us a more seasoned industry veteran at such a young age and we'll show you a liar. Josh Peskowitz, editor-turned-fashion-director, may know more about men's clothing than anyone on this list. Peskowitz is a menswear chameleon of sorts, pulling off different style after different style in almost every picture that's taken from him. That fact speaks a lot to his eclectic pedigree and is proof that some guys just know what they're doing. Pesko's most impressive sartorial feat may have been a few years ago when a broken foot forced him to rock a cane during Fashion Week. And, you know what, he still killed it. Like The Sartorialist once said, "limpin' aint easy."