In 1944, Paul Van Doren dropped out of eighth grade. Like most fourteen-year-olds, he didn’t particularly like going to school. But unlike most teens, he was interested in–and had a knack for–gambling at horse races. His disapproving mother ordered him to instead find legitimate work at a shoe manufacturing company, Randy’s, in his native city of Boston.

The Off-The-Wall History of Checkered Vans
The House of Vans, the first standalone store in Costa Mesa, California, in the early 1970s.

Paul eventually worked his way up from sweeping floors and making shoes to a role as the Executive Vice President for Randy’s. In 1965, the company sent him to California to turn around a failing Randy’s branch. Paul moved, along with his brother Jim and their families, to Anaheim. Not only did the brothers save the factory, it went on to function better than the Massachusetts location—in just eight months to boot. Three months later, Paul decided he wanted to start his own shoe brand.

On March 16, 1966, at 704 East Broadway in Anaheim, California, the Van Doren brothers joined forces with Gordon Lee and Serge D’Elia to open the first VANS store (then called the Van Doren Rubber Company), where they both manufactured shoes and sold them directly to the public. On that first morning, twelve customers purchased VANS #44 deck shoes, which are now known as the “Authentic.” With the success of their business, a second VANS shop opened in Santa Monica within a year. The #44 deck shoe became popular with the Santa Monica High School (SAMOHI) surf and skate culture.

The checkerboard pattern and the #98 Classic Slip-On style actually existed separately for a bit before coming together to form the iconic shoe. In the late ‘70s, Paul’s son Steve noticed a trend with teen skaters. They used black permanent marker to color the rubber midsole of their shoes in a checkerboard style. Inspired, Steve further developed the idea by moving the pattern to the upper canvas segment of the shoe.

At the same time, the black-and-white pairing of the checkerboard came to represent something more significant than just DIY culture. In the ‘70s, subcultures in London embraced the second wave of Ska music. Punks in particular isolated the raw rhythms and speed and mixed them with the Caribbean melodies. This particularly politically-charged second wave came to be called the “Two Tone Wave” because of its combination of typical “white” and “black” sounds. The VANS checkerboard shoe became a choice fashion accessory for those amongst the subculture, representing the breaking of racial barriers and replacing them with unity.

However the #98 checkerboard’s mainstream popularity really took off through the 1982 film Fast Times at Ridgemont High—more specifically, with Sean Penn’s lovable slacker character, Spiccoli. Universal Studios had requested a selection of VANS shoes for the film from the corporate office. The Van Dorens sent over options, not intending to promote the checkerboard slip-on specifically. Sean Penn picked the style for his character, for whom it became a representative icon. When audiences saw the preview–in which Spiccoli hilariously uses the shoe to whack himself in the head–customers’ own requests for the style went through the roof.

Since then, the #98 checkerboard slip-on has been seen pretty much anywhere and everywhere: on the feet of skaters in Santa Monica and music fest fanatics alike, sported by off-duty models and even on the red carpet. It’s unusual for an article of clothing to both appeal and be accessible to two seemingly polarized groups. Yet the #98 checkerboard slip-on exists in that middle section of the Venn diagram. Perhaps, then, the groups aren’t so different, or can at least find more commonalties than previously thought. And perhaps fashion is that key.

[+] VANS

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Featured image © Lena Orwig. Additional images © TIMEThe Hustle, and The Other Side of the Pillow. All Rights Reserved.

Sources: Smith Journal,, and The Hustle.

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