Film: The Aviator
Year: 2004
Signature Look: DEFINITELY NOT a Guy Who Pisses In Jars

DiCaprio's Howard Hughes wears the leather flight jacket extremely well, and stands out as one of his best roles ever. He looks stunning in a tux and wore double-breasted suits with pure aplomb. It's no surprise that designers like N. Hoolywood's Daisuke Obana channel him in aviation-inspired fashion collections. In fact, his great style makes his fall from grace more tragic, while his Indiana Jones-esque attire in the film's ending shows that even the most well-dressed man can still be fighting demons underneath his tweed jacket.