36. Tyler, The Creator
Height of Style: "Yonkers" video
Signature Look: Supreme caps, printed shirts, tube socks, Vans
Great style isn't only about the clothes one wears, it's about how cool one looks doing it. That usually means looking like you don't give a fuck, which is something Tyler, The Creator does extremely well. His laid-back California skater style (combining bold printed shirts, denim cut-off shorts, tube socks, Vans, and Supreme snapbacks) has legions of fans buying up racks of clothes on Fairfax to look just like him and his Odd Future mates.