Year: 1987
Sneaker: Nike Safari

Biz Markie was an unlikely style icon-a hefty rapper who made music with his mouth. But thanks to the back of his record Goin' Off, he will be forever linked with 1987's Nike Air Safari, a Tinker Hatfield creation that merged sports with luxury thanks to a deer leather upper and ostrich-inspired "Safari print" trim. Beats being remembered for pickin' boogers.