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On Wednesday, Vans will turn the big 5-0. That’s right: the sneaker of choice for the young at heart is solidly middle-aged. What’s its secret for looking fresh as ever, you ask?

“People have long sought out Vans for many reasons,” says Steve Van Doren, 60, the brand’s vice president of events and promotions. “The great functionality for skateboarding, the ability to use the shoes as a canvas for art or to wear to a concert.”

Founded by Van Doren’s father, Paul, and three business partners, the company opened its first retail store in Anaheim, Calif., in 1966. By the mid-’70s, the kicks were en route to cult status, appealing first to SoCal skateboarders — who coveted the brand’s signature, traction-providing waffle soles — and then to practically everyone who saw Amy Heckerling’s 1982 classic “Fast Times at Ridgemont High.”

“Everyone around the world knew what Vans were after that film,” says Van Doren of the era-defining movie, starring Sean Penn as Jeff Spicoli, a stoner and surfer who wears a certain pair of checkerboard slip-ons.

In the decades since, the company’s footwear has become a cultural mainstay. Although collaborations are frequent and customization has been a popular component since the beginning, the core lineup remains the same. Here, Van Doren walks through the origins of Vans’ most iconic shoes.

  • Authentic, 1966

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    “Vans style #44, known today as the Authentic, was the very first Vans shoe ever designed,” says Van Doren. “[It was] the No. 1 selling shoe in 1966 and is still the No. 1 style across the world today.”

  • Era, 1976

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    According to Van Doren, the Era, formerly style #95, was designed with the help of famed skateboarders Tony Alva and Stacy Peralta. “The shoe has a padded collar that provided more protection and durability for skateboarding, and the multipanels allow for an array of different color combinations,” he explains. “It quickly became the shoe of choice for generations of skateboarders.”

  • Slip-Ons, 1977

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    So, how did the checkerboard slip-ons, a k a style #98, end up in “Fast Times at Ridgemont High”? “Sean Penn visited the Vans Santa Monica, Calif., store and purchased a pair that he wore on set,” Van Doren recalls. “The director took notice and asked Vans for additional pairs so they could be part of Spicoli’s wardrobe.”

  • Old Skool, 1977

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    “The Old Skool is Vans’ first skate shoe that incorporated leather panels for increased durability,” says Van Doren on style #36, which was also the first to feature the well-known side stripe. “What started as a random doodle illustrated by my father was originally referred to as the ‘jazz stripe,’ and has become the recognizable hallmark of the Vans brand.”

  • Sk8-Hi, 1978

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    “The Sk8-Hi was Vans’ first high-top shoe and was designed as a way to answer the demands of skateboarders who were looking for added durability and ankle support as the sport became more technical,” Van Doren says. “It was the second style to feature the Vans side stripe [the first was the Old Skool, in 1977].”

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