40. J-Money
When I say J-Money, I'm referring to the label, but I'm really talking about Jamie Story, one of the kingpins of New York streetwear. The veteran graphic designer is responsible for some of the most memorable hip-hop artwork (Big L, rest in peace); he embodied the New York urban aesthetic at the turn of the millennium. But it was his ties to the local skate, street, and sneaker community that established Jamie as one of the protégés of third-wave streetwear. His "King of NY" tee is still one of the greatest shirts of all time and it was very much a literal statement.