6. Lil Wayne
Lil Wayne shows glimpses of becoming a style savant, and then he wears furry boots; fucking up his whole swagger in the process. The New Orleans native has shown a genuine interest in the skate world—even launching a skate brand, Trukfit, in the process. But if he didn't dress like a walking-ad for stores that mall-grabbing kids shop at, and wore some genuine, understated skate brands like Supreme, Raw, or Palace, he might harness a stylish formula that's equivalent to his spazzed-out efforts on the mic.