22. Fabolous

Complex says: Since Fab jumped on the scene in '01, he has always kept it together rocking fresh clothes and fresh kicks. He may have gotten busted with some fakes on Bobbito's ESPN show but even MJ missed a game winner or two. No doubt Fab consistently comes with the heat whether he was rocking Jordan X "Chicagos", V "Quai 54s", and just about anything else early.