Film: Romeo + Juliet
Year: 1996
Signature Look: Angst, Personified

Kym Barrett 100% bodied the costume design on this modern reinterpetation of Shakespeare. For centuries, dudes have rolled their eyes in English class thinking Romeo was some punk bitch with a corny hat and stupid tights trying to bang this Capulet chick, then Baz Luhrmann comes along and adds guns, explosions, and John Leguizamo, and all of a sudden Shakespeare becomes awesome. Romeo goes from a pre-LiveJournal sad sack to a troubled gangbanger with a penchant for floral patterns and chain smoking. It was a very visceral way of telling kids "hey, Romeo was like 'Drake' before 'Drake' existed," and the outfits complemented it perfectly.