20. Crooks & Castles "Medusa"

Released: 2007

Is this the first Crooks tee? No. Is it the most iconic? Maybe, but it's definitely the dopest. Roman iconography mixed up with a red and green bandanna can't really be beat.

YOU AUGHTA KNOW:
Jay-Z was an early supporter of Crooks and helped launch the West Coast brand on the international stage.