Character: Guybrush Threepwood
Video Game: The Secret of Monkey Island (1990)

LucasArts may be defunct, but Guybrush Threepwood is immortal. The point-and-click adventure star is remembered not only for his in-game hijinks, but his appropriate flood pants. After all, he spends a lot of time on the high seas. While award-winning designer Thom Browne made a name for himself by pushing the shrunken trouser silhouette in his menswear collections, we should give credit where it's due, and acknowledge that Threepwood was already up on that long before Browne's first collection. Perhaps the designer was a secret PC gamer?