Film: Inception
Year: 2010
Signature Look: Ambiguous Futuristic Mastermind

Dom Cobb is one of DiCaprio's most awesome roles, but it's a far cry from one of his most stylish. While he holds his own in leather jackets and slim suits, he's easily outshined on the screen next to dudes like Joseph Gordon-Levitt (who kills in in a perfect brown leather jacket and expertly-tailored three-piece suit) and Cillian Murphy, whose double-breasted suit blows away DiCaprio's peak-lapeled, single-breasted suit. Well, you know what they say... haters gonna hate.