38. Crooks & Castles "High Society"

Released: 2005

Streetwear brands often try to take the piss out of high-fashion brands in their designs, and often put up a brick. Not the case with this Crooks tee.

The paparazzi shutterbugs caught Jay-Z on the street rockin' this tee, which heavily increased the demand for the T-shirt months after it dropped.