1. Checkerboard Slip-On (Black/White)
Year Released: 1979
This shoe is what made Vans become a global brand and the story behind it is even better. When Steve Van Doren was in high school, kids were drawing checkerboard patterns on their shoes. Steve came home and told Paul Van Doren and the next day they were screen printing the first checkerboard Slip-On. But what really made this shoe special was when Jeff Spicoli (Sean Penn) was taking bong hits and hitting himself in the head with the checkerboard Slip-Ons in Fast Times At Ridgemont High. From that point forward Vans was a brand that represented the So Cal Surfer dude and the attitude that came with it.