Boyz N The Hood (1991)
Director: John Singleton
As kids, the characters of Doughboy, Dookie, and Tré were fresh (check that cap and "Beat It" shirt, above). When they grew up, they implemented mesh shirts, ill prints, snapbacks and caps of all sorts, and even that infamous black-and-yellow contrast-sleeve buttondown from the movie poster. When you roll with a crew that looks this tight, you better know, show, and care about what's going on in the hood.