The Endless Summer (1966)
Director: Bruce Brown
This seminal film has inspired so many surfers to hit the waves, and is a great guide on how to rock a great-fitting pair of boardshorts. Also, we definitely have to give props to Robert August and Mike Hynson's off-the-beach style. With indigo tees, smart white plimsolls, buttondown shirts, anoraks and suits, these guys were gentlemen, not dudes. Today's beach bums should take a few style cues from these OGs and step up their casual game.