40. St. Alfred "St Alfred YSL Logo"

Released: 2006

Chicago's premier streetwear/sneaker shop (which was created by steetwear visionary Ian Ginoza) has kept industry trendsetters like Lupe Fiasco and Kanye West laced for years. When the store decided to do a take off on YSL's signature initials, they brought it forward.

The back of the tee reads "HI"—a shout to Ginoza's Hawaiian location, Kicks/HI.