"Joe" (Joseph Gordon-Levitt)
When it comes to outerwear, JGL's character, Joe (how fitting), seems to be darting between two dueling icons of the 1950s, Marlon Brando and James Dean. When sporting his black leather moto jacket, he almost resembles Johnny Strabler, Brando's character from The Wild One—albeit without his name on the lapel, the plethora of zippers or the tilted vintage motorcycle cap. Other scenes, including the one where Mr. Gordon-Levitt's character encounters Mr. Willis (playing his older self), feature him in a Baracuta-style jacket that is reminiscent of James Dean's iconic duds in A Rebel Without A Cause. His attire underneath the outerwear is fairly consistent with the '50s bad boy, but is also skewed to the Patrick Bateman-esque shirt-and-tie combos that were especially popular in the '80s. That look came along again in the early 2000s, when a new generation of pre-recession bankers reigned supreme for a good 8 years or so—maybe they were actually time traveling mob hit men all along?