The Sk8-Hi officially arrived in 1976 and was first called “Style 38,” as Vans used to number its shoes in lieu of properly naming them. (Its modern moniker was introduced in 1995.) But this particular style's story actually begins with the Old Skool, “Style 36,” and is deeply rooted in the company’s history with skateboarding. Skaters already loved Vans’ sneakers for the rubber soles, but these weren’t expressly designed for the sport. In 1977, that changed with Style 36, which featured a new leather-and-canvas construction that really lent itself to wear and tear. This came out around the same time as the Era, Vans’ first designated skate shoe.

While these releases were a pretty big deal, skateboarders’ experiences with the shoes led the brand to realize there was an important element missing from them: ankle protection. Vans already made separate ankle guards that could be Velcro-ed around the ankles, Van Doren recalls, but there was a need for shoes that accomplished this protection, too. So the brand released its mid-top called Style 37, but that wasn't enough. “That’s where the Sk8-Hi comes in,” explains Van Doren. “[Skaters] liked the padding in the ankle guards [sold separately], so we took that material and designed a high-top with padding.”

For Style 38, Vans kept the two features of the Old Skool that skaters loved: the brand’s signature waffle sole and its canvas-leather construction. The original Style 38 came in navy blue leather with light blue canvas, cinnamon-hued rust leather on rust canvas, and brown leather on beige canvas. But customization was huge for Vans in its early days — shoes were even sold individually instead of in pairs, so you could mix and match colors. This was especially useful for skaters, since they tend to wear out one shoe before the other.

Since the brand's mid-'60s inception, customers could bring a print or fabric to the Vans warehouse and have it turned into a shoe. Others took a more DIY approach, taking advantage of the additional blank canvas on the Sk8-Hi’s side panels to doodle freely. "There is so much real estate on a Sk8-Hi that you can have a really beautiful print story; there's [a design] opportunity that you don’t get on a slip-on, because of how many panels there are [on the Sk8-Hi]," explains Dabney Lee, Vans’ senior director of merchandising for Classics footwear.