1. Colorful Polo shirts
“Back when they thought pink polos would hurt the Roc…”
Kanye West came into the game doing his own damn thing. In a hip-hop fashion environment that praised baggy jeans, throwback jerseys and the oversized tee, Kanye pulled up to the scene in pastel Polo shirts. He put hip-hop on to the preppy look, and it hasn't looked back.