Neighborhood: Santa Monica
Signature style: Tons of Supreme; dressing like a skater (who actually skates).

If you've followed the story of Earl Sweatshirt over the past couple years, you'll know his personal life has been just as intriguing as his rhymes. The son of South Africa's poet laureate, Earl disappeared at the peak of his hype to attend a program for misguided youth. Upon his return in 2012, Earl not only went on a lyrical tear, he also upgraded his style.

In an industry full of skater wannabes, Earl has legit credibility, and his friendship with Jason Dill confirms that. Just like a lot of his skate counterparts, Earl digs a healthy amount of Supreme, tie-dye shirts, bucket hats, and anything that's comfortable when tearing down stages or skating down the block. Still, the best part of Earl's style is that he dresses like himself, and he has only just begun.