The movie: Step Brothers (2008)
The player(s): Will Ferrell and John C. Reilly

In the right context, this sartorial statement is totally spot-on. But there's a difference between "vintage" and "old." And just because you've been wearing the same Star Wars T since high school doesn't make it vintage. In Step Brothers, Brennan (Ferrell) and Dale (Reilly) duke it out in more ways than one—including an unsaid competition for who can wear the oldest/least stylish T. It's a toss up in their video for "Boats & Hoes," though given the Miami Vice vibe, maybe they're more fashion forward than meets the eye. (The Nina, the Pinta, the Santa Maria...)