50. Leopard Print 5 Panel, 2011

Tyler, The Creator donned the now famous "Feathers Cap" in his notorious music video "Yonkers," but when he wore this leopard brimmed 5 panel at the 2011 MTV VMA's, it signaled a tipping point in Supreme's legacy. In this case, it's not so much the hat itself that earns it a spot amongst the Top 50, but simply the mass media context in which it was consumed by culture at large. In the weeks following the VMA's the hat would drop and sell out in mere minutes (not a first for the label, of course) and would be seen on the heads of both diehards and those who had never heard of Supreme before. For better or for worse, that makes this hat special.