Progress Report: Leonardo DiCaprio makes a case for the slip-on sneaker. His predilection for washed denim suits him well, especially in the warmer months. He also isn't afraid to take style risks, like tying his jacket around his waist.
Needs Improvement: DiCaprio should lose the newsboy cap as soon as possible. There are also far better ways to go incognito rather than constantly pulling hoods over your head. Life isn't Assassin's Creed.