14. Trinidad James
Hypebeasts, we know 'bout cha. Trinidad James may be a relative newcomer to the hip-hop scene, but it's clear that he's already making waves. Whether he has any staying power has yet to be determined, but what's evident from the get-go is that he has serious style. Sporting animal print, jewelry, bright colors, and Supreme gear (way before the plebeians), Trinidad James is a serious contender as one of the best-dressed rappers right now. Even though he's essentially channeling Deion Sanders' '90s steez, it doesn't make it any less awesome.