45. Del the Funky Homosapien
Height of Style: The 90s
Signature Look: Backpack, lip ring, T-shirt head wrap
Before Tyler, The Creator and Odd Future did the whole skate/hip-hop style mash-up, there was Del. His rap style remains unlike anyone else, as does his fashion sense. You may not see many lip rings in these streets these days, but the sentiment lives on.