Design Credits: Public School and Black Apple

Cutting his teeth as a designer for Sean John, that's where Maxwell Osborne met co-designer Dao-Yi Chow. Together, they set out to create high-end clothes with a gritty New York edge through the label Public School, and then established its streetwear-oriented offshoot, Black Apple.

The spirit of New York's downtown bohemian scene and middle-finger-to-the-world delinquency perfectly rings through Osborne and Chow's designs, and while they're both two stylish guys in their own right, Osborne's drapey, dark, aesthetic and trademark dreads make him a sartorial force to be reckoned with. Having just launched a denim line and a collaboration with the New York Knicks, expect more great things to come from this guy.