Movie: Fast Times at Ridgemont High
Sneaker: Vans Slip-On

"That was my skull!" Jeff Spicoli remains a role model — entering fast food outlets shirtless, ordering pizzas in the classroom and wearing vulcanized Vans long before they went epidemic beyond the west coast. The checkerboard pattern became a bestseller and when Jeff smashes his shoe against his head straight out the box post-bong, classic status was conferred.