The iconic Vans Classic Slip-On 'Checkerboard' was created in the late 1970s by Steve Van Doren after noticing that teenage skaters were coloring checkerboards into their white rubber midsoles with black pens. The shoe’s real breakthrough came via Sean Penn’s character Jeff Spicoli in the 1982 movie Fast Times at Ridgemont High, with the movie's trailer featuring the loveable stoner hitting himself over the head with his new pair of checkerboards after taking a rip from a bong.
