Behind the Hype: How the Vans Old Skool Influenced Skate, Art, Streetwear, and Beyond

Vans continues to be an influential brand within skateboarding, street fashion, art, and popular culture — its iconic red logo is instantly recognizable across generations. However, one silhouette kicked the brand into high gear in terms of global reach and covetability amongst discerning footwear aficionados. The Vans Old Skool, accented with Vans’ signature Sidestripe, established the footwear label’s incomparable legacy. Since the release of the shoe, Vans has gone on to demonstrate longevity amongst various cultures, all the while being hailed by celebrities including Justin Bieber, A$AP Rocky, Travis Scott, and Frank Ocean, as well as skaters, artists, fashion designers, and the youth culture. In the latest installment of Behind the Hype, Hypebeast recounts the rise of Vans and the various cultural touchstones the classic Old Skool has become a part of.

The Vans story began when brothers Paul and James Van Doren, along with Gordon Lee and Serge Delia, partnered to start the Van Doren Rubber Company. The brand released its first skate model, the Era, in 1976 as part of the Off the Wall line. About one year later in 1977, Vans added the Old Skool (known initially as Style 36), followed by the Sk8-Hi (1978) and Slip-On (1979) models. Each original shoe displayed the red Off the Wall heel tab that can still be found on contemporary models, but the Old Skool sported a new look and durable suede construction that caught the attention of skaters everywhere. It debuted a never-before-seen Vans signature Sidestripe, drawn by Paul Van Doren himself. Paul gave the doodle to Vans’ in-house designer and patternmaker George Greenwood, who then integrated it into the Old Skool’s design and nicknamed it the “Jazz Stripe.” This identifiable design feature as well as unique leather panels in the toe and heel of the shoe made it an instant fan favorite for its style and durability.

The Old Skool is a shoe that both proponents of popular and underground culture can identify with, and its timeless design combined with an affordable price point cemented the model as a go-to staple. Not only is it fit for skateparks and punk rock concerts, but it’s also been worn on red carpet premieres by some celebs, proving the brand’s widespread influence. The silhouette became an immediate classic in the early 80s as it was worn by skaters, BMXers and American teenagers alike. The influence of the shoe’s design and construction continued through the 90s, as Vans became a globally recognizable brand and sponsor of the alternative music festival Warped Tour, later renamed as “Vans Warped Tour.”

Given that the Old Skool is a simple timeless design rooted in the history of skateboarding and skate culture, it later went on to become the ideal canvas for customization and collaborations. Beginning in the late 60s, Vans uniquely began allowing their customers to create custom one-of-a-kind shoes with their own fabrics because they owned and operated their own factories in Southern California. This early customization practice was used by individual customers and businesses alike, setting a foundation for official and formal collaborations that began as early as the 70s. By the late 70s, adolescents began personalizing their Vans with hand-drawn artworks, leading Steve Van Doren, son of co-founder Paul, to open design contests between wearers. As time progressed, Vans maintained the essence of the Old Skool and many of its other models through general releases while also putting modern spins on colorways and even collaborating with artists, such as Kaws, Stash, Futura, and more.

In 1996, then Supreme Design Director Brendan Babenzien introduced the Supreme Old Skool collection. The highly-coveted shoe was a golden co-sign by one of skatewear and streetwear’s most influential brands. It was a three-colorway collaboration that further cemented Vans’ enduring appeal in fashion and footwear culture — and set the tone for 10 more Vans x Supreme collaborations to come, dropping seasonally to this day. Taking collaborative projects a step further, Vault by Vans opened in 2003, ushering in a period of conceptual high-end collaborations, such as those with Palm Angels, UNDERCOVER, Engineered Garments, and more. In 2009, Vault by Vans released a 20th Anniversary Reissue Pack for legendary skater Ray Barbee that included the Old Skool ‘92 Reissue LX model, which was designed to emulate the overall form and details of archival 90s models of the Old Skool. It was this model that set the foundation for today’s Old Skool model, paying homage to its heyday in early 90s street skating.

Shortly after Vault by Vans launched, Vans penned another chapter to its story with the release of the Syndicate Line which granted non-traditional artists and cultural rebels the opportunity to showcase their eccentric designs on various Vans silhouettes including the Old Skool. Not only were Vans and the early Old Skool model endorsed by the biggest brands, but street culture figures such as Jason Dill, Shawn Stussy, and Tyler the Creator also created their own reimaginings of the sneaker.

The Syndicate Line ran for ten years, among other special Vans projects, including Vans Customs which invited fans to personalize their shoes online — an option that is still available on the Vans website. A Simpsons collaboration featuring an array of artists and other partnerships came to fruition as the brand’s cultural reach grew. The Old Skool has been revamped in many ways as well. The Blends “Bones” Old Skool emerged in 2014, the BMX and Deconstructed Old Skools dropped in 2019, and the 2022 Knu Skool model later dropped — a Vault by Vans collaboration with Imran Potato that reintroduced the 1998 Vans silhouette. Originally designed to reimagine the Old Skool at the end of the 20th century, the Knu Skool captures 90s street style with its puffed-up tongue, ankle collar, and three-dimensional beveled Sidestripe, reflecting how influential late 90s skateboarding was to men’s fashion.

The Vans Old Skool has seen it all — it’s been reinterpreted in satin, corduroy, sherpa, and even fully encrusted with Swarovski crystals — but the heart of the shoe and its original structure remains. What began with creating a more durable skate shoe with suede construction in 1977 has persisted to drive culture for decades, and the influence of the Old Skool continues to echo within street and skate culture far and wide.

To learn more about Vans and the history of the Old Skool shoe, watch the video above. For a closer look at the models mentioned and to check out current selections, head over to Vans’ official website.