34. No Mas "Strawberry"

Released: 2005

No Mas always had fun cranking out designs inspired by the sports world, but Chris Isenberg and crew didn't even try to check their swing when they dropped this classic. The Straw and Nancy Reagan's infamous phrase are like two ironically juxtaposed peas in a pod.

YOU AUGHTA KNOW:
Nothing's better than real life—the shirt was inspired by a wristband Strawberry actually wore back in the late '80s.