Film: Gangs of New York
Year: 2002
Signature Look: Street Rat Sprezzatura

Amsterdam has that "unstructured but dressed up" look down centuries before #menswear did. Plus, we don't think anyone else wears the cabbie-style cap better. He proveshimself a style icon when, in true punk fashion, he dip-dyes his shirt in rabbit's blood, no doubt creating the DIY movement and inventing colorblocking at the same time. Today's gangsters... they have it so easy with their bandanas and colors.