18. Tyler, The Creator

OFWGKTA's de facto leader has always had a penchant for weird shit. Whether it's tye-dye T-shirts with cats or upside-down crosses, to covetable Supreme crewnecks and leopard-print five-panels, he's rocked it all with knee-high tube-socks and Vans. Combine that with his controversial lyrics and recent vandalism arrest, and it seems Tyler is poised to become the new face of teenage rebellion.