The humble Sperry boat shoe was featured prominently on the cover of “The Official Preppy Handbook” in 1980, and author Lisa Birnbach deemed it a defining piece of the preppy uniform.

It wasn’t the first time the classic look dominated the cultural conversation, of course. John F. Kennedy, whose effortlessly cool, coastal-chic style made him a preppy icon in the early 1960s, helped establish the brand’s relationship with American aristocracy and Ivy League trendsetters.

“The boat shoe has always been a symbol of classic American prep. It is casual but refined, coastal yet timeless,” said Preston Konrad, lifestyle expert and founder of Preston Lane. “Sperry made it iconic, and it became part of the uniform for a certain kind of East Coast lifestyle.”

Now as preppy makes a notable comeback and the fashion tides shift again, the Sperry Top-Sider is being embraced by a new generation of style arbiters — thanks to the boat shoe resurgence on the runway, a newfound following among the street-style set and the growing popularity of sailing. Celebrities from Jennifer Garner to Jennifer Lawrence to Emma Corrin have all stepped out in different iterations throughout 2025.

And the increased interest is translating into sales gains, with Circana research showing that overall boat shoe dollar sales were up 28 percent during the first half of the year compared to the same period last year.

“I’m seeing it styled in more intentional, fresh ways, pairing it with vintage, tailored pieces, or even streetwear. It is less about recreating a traditional preppy look and more about reinterpreting heritage for right now,” Konrad said. “It has been polarizing at times, but I think that’s starting to shift.”

Bruce Pask, senior director of men’s fashion at Saks Fifth Avenue and Neiman Marcus, said the boat shoe’s return is another example of fashion’s obsession with nostalgia.

“It speaks to an aspirational American mood and the midcentury collegiate lifestyle where this fashion phenomenon began — with its focus on camaraderie, leisure, sports and academia,” he said. “College years can often be viewed as a simpler time, an idealized past.”

Boat shoes reemerged on the fashion scene after appearing on Miu Miu’s spring 2024 runway and quickly spread to collections from major designers like JW Anderson, Jacquemus, The Row, Burberry and Prada.

“That moment kicked off a real frenzy for the ‘preppy’ wardrobe essential and an abundance of great new versions, colors and materials in boat shoes, which our customers have embraced,” Pask added.

Across fashion, the preppy trend quickly began to build, with rugby shirts, khakis and button downs seen prominently across the spring ’26 men’s collections. And in the season’s most-talked-about show, Jonathan Anderson put his own unique preppy spin on Dior’s signature looks, fueling tons of interest among buyers and consumers alike.

“Right now, there is a big return to the classics happening across fashion and home, and preppy style is at the center of it. People are craving timeless, heritage- inspired looks that feel grounded and familiar,” Konrad noted.

Sperry — and the boat shoe silhouette in general — fit squarely in that category, according to Jian DeLeon, Nordstrom’s men’s fashion director.

“The boat shoe is a prep style staple. But it’s also been synonymous with laid- back elegance and an aspirational life of leisure. Even though they have laces, most can be easily slipped on or off,” he said, noting that the style’s renaissance is still in its early stages with mainstream consumers.

In February, the department store teamed up with Sperry for its “Make Room for Shoes” program, a monthlong spotlight that gives Nordstrom customers access to limited-edition footwear styles designed specifically for the retailer.

At Nordstrom and other retailers, the comfort elements of the footwear are a big selling point. “In the age of comfort where slip-on shoes are the most popular styles out there, the boat shoe is a perfect addition to one’s wardrobe both for men and women,” Ellen Lynch, professor and founder of the footwear and accessories department at the Fashion Institute of Technology, said in an interview. “Perhaps the only difference is in the materials used and the sleekness of the more modern design.”

It’s this classic-yet-modern mix that allows Sperry, the boat shoe originator to remain relevant. Under Aldo Group, the brand has eschewed traditional celebrity partnerships to focus on collaborations across a diverse range of categories.

In the women’s market, Sperry’s slimmed-down boat shoe with Aritzia was an instant sellout, leading to multiple restocks. “It’s particularly ironic for me, as I wore [Sperry boat shoes] regularly in the 1980s in university,” said Brian Hill, founder and executive chair of Aritzia, which, like Aldo Group, is a Canadian-based company. “We have partnered with [Aldo founder and executive chairman] Aldo Bensadoun as he has advised Aritzia on our board for 15 years. It’s a pleasure to now partner with Aldo on such an exciting brand as Sperry.”

The brand has also teamed up with Monse, J.Crew and Todd Snyder, among others. “Sperry has always had a place in my life — it’s a staple where I’m from and has served so many generations of people looking for the perfect combination of style and function,” said Brendon Babenzien, men’s creative director at J.Crew and a Long Island native.