The Topsider, the infamous leather moccasin-style shoe initially intended for sailing that became a 1980s fashion item, capitalizes on retro-era popularity among Gen Z.

Lisa Birnbach’s ‘The Official Preppy Handbook’ published in 1980, was the ultimate guide to obtaining the look and mannerisms once held by an elite segment of American WASP society, for the style curious gravitated towards the preppy look for its fashion cred in the booming eighties excess.

The tome detailed what to wear: Izod Lacoste, Brooks Brothers, L.L. Bean, and the de rigeur shoe, the Sperry Topsider. Fast forward to over 40 years later when the uniquely American leather moccasin with a rubber non-slip sole has endured and is once again finding itself at the center of popular style. This time around, helping earn style cred is menswear designer Todd Snyder thanks to a new collaboration, Sperry X Todd Snyder. To celebrate the tie-up, Sperry and Snyder co-hosted a cocktail on Manhattan’s most popular riverboat establishment, Grand Banks. FashionNetwork.com was there to catch up with the buzzy creative and the shoe company, which will celebrate the shoe’s 90th anniversary next year.
 
For Snyder, it’s not surprising. “When we started this project a year-and-a-half ago, I felt the 80s and 90s coming back. A lot of luxury players have also been revisiting the style. I looked back to my childhood and my father’s closet, and this American luxury from the 80s moment is happening now. This is my wheelhouse; I was in high school in the 80s, and my buddy Matt wore Topsiders. I thought they were really cool, but I got a white pair to be different and thought ‘nobody has these,'” Snyder told FashionNetwork.com in between grooves from DJ Lucas Walters adding, “The return of the shoe comes from a feeling or emotion to return to this luxury American country club but in a relevant way with a twist to something that has been done before. For me. I must change something 30-40 percent.”
 
According to the designer, one of the three styles is white in honor of his first pair. But today’s version pairs Sperry’s signature razor-cut Wave-Siping technology with a thicker Vibram outsole, making them more comfortable and more supportive than the original.

“The nice thing about Sperry is it’s purely American, like the sneaker or cowboy boot, for instance. Not many things can claim that. As an American designer, I know these shoes, which were beloved when I was growing up and becoming a fashion designer. They made an impression on me and gave me a reference,” he continued, hinting that another uniquely American collaboration he would love to do would involve interiors.
 
Jonathan Frankel, president, Sperry, agrees that the shoes are ripe for a moment today when the modern prep and nostalgia are big among Gen Z.

“The 80s preppy fashion was anchored around private clubs and a lifestyle you admired and wanted to look the part. Today, we see an interest in golf and tennis culture and coastal and cottage lifestyles in a younger demographic. People tend to gravitate towards the coast to take holidays, unplug and relax. The brand is strong in those environments where they go from day to night,” he said.

It’s also an upgrade from athletic shoes. “During the pandemic, everyone had 15 pairs of sneakers; now the younger customers are looking for something relevant from a fashion point of view that is also easy and comfortable,” he said, equating Sperry Topsiders to a favorite pair of jeans.

Frankel also praised Snyder’s talent for his vision in rejuvenating the style, modernizing it to attract a new customer and demographic in a way that is not forced.

“Todd has a knack for doing that,” he added.
 
The collection, released earlier in the month, will be accompanied by a campaign shot in New York’s Lower East Side neighborhood by Jeremy Mitchell and featuring men’s style gurus Jake Woolf, Brynn Wallner, and Jordan Page. The styles come in white, tan, and gray and retail for $220. They are available on Sperry.com, Todd Snyder.com and Todd Snyder stores.

On the heels of this collaboration is a series of monochromatic textured suede Topsiders in partnership with streetwear brand CNCPTS dubbed ‘Dawn to Dusk’—in reference to styles that come in colors mimicking the various shades of the sky—which retail for $150 and will drop exclusively on cncpts.com and sperry.com and in-store in time for Memorial Day weekend with a wider release to follow.

The pairing proves the style has endured past the hallowed halls where Muffy and Chip once reigned.

“The collaborations are the jewel in the crown,” said Frankel, noting that being creative and authentic usually trumps the typical commercial product concerns. The brand was recently acquired by Authentic Brands Group, a global brand development, entertainment, and marketing platform, with Aldo coming on as Sperry’s North American operating partner for wholesale, e-commerce, and store operations, as well as the brand’s partner for footwear design, production, and distribution globally. Thus, the current buzz is undoubtedly welcome.

“Many generations recall that their favorite shoes were a pair of Sperry, so it’s been lovely to see how welcoming the next generation is to the brand. Doing collaborations in a creative way is exciting to them,” he said, adding that there will be more collaborations upcoming, which could also help Sperry regain traction in other areas of footwear.
 
Frankel also noted the shoes are here to stay beyond summer 2024 and on trendy bar boats.
“We will see them everywhere near the city or the coast for the next couple of summers. Sperry Topsider will be relevant in the fashion space when done with authenticity; it’s never forced, and we don’t have to be ‘too cool for school’ when you are an originator of something. We remain humble and stay true to the brand, and we are welcoming, so it naturally invites more to participate.”
 
Indeed, today’s world is inclusive and a far cry from the one where Birnbach’s characters fondly expressed NOKD, aka ‘Not Our Kind, Dear.’ That was so 1984, and these Sperry’s Topsider are decidedly 2024.