Preppy was a uniform; it was also not hip-hop. Kanye played with both of those rules. Preppy became a way to show his individuality, with him rocking the flashiest clothes possible while still wearing collared shirts. It wasn't a way to blend in, it was a way to stand out. Hip-hop's fashion possibilities were broadened in turn.
16. Kanye with the popped collar on the pink Polo in "All Falls Down."