Film: The Basketball Diaries
Year: 1995
Signature Look: Heroin Chic, obviously

Jim Carroll starts off as a respectably preppy dude until he falls harder into drugs and begins to resemble a shell-shocked Vietnam Veteran. His cut-off basketball shirts, worn-in fatigue jacket, and ripped-knee jeans might have been grunge style staples, but here they perfectly show his descent into darkness... but is it super messed up for us to admit that he kind of looks cool that way?