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Reviving Sperry

After the preppy heyday of the 1980s, the Sperry Top-Sider became decidedly uncool. Now, a new generation of shoppers has discovered the brand and made it hip again.

Michelle Smith, the designer of Milly, and Craig Reingold, president of Sperry, at a party in February celebrating their collaboration. Michelle Smith, the designer of Milly, and Craig Reingold, president of Sperry, at a party in February celebrating their collaboration. (Handout)
By Christopher Muther
Globe Staff / April 5, 2012
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LEXINGTON — The 1990s were not kind to the Sperry Top-Sider.

The iconic boat shoe blazed to the fashion forefront in the early 1980s after gaining fame and acclaim in “The Official Preppy Handbook” and countless John Hughes films. But by the end of the decade, the New England-based shoe had fallen out of favor, the sartorial equivalent of Wang Chung.

“It was clearly a declining brand,” says Craig Reingold, president of the Lexington-based Sperry. “That was when they were cheapening the product. They were using a lesser grade of leather. You can’t do that.”

Making matters worse was the fact that no one knew quite how to market the shoe in the 1990s. “Preppy” was passe. “Top-Sider” was dropped from the company name in hopes of distancing the brand from the 1980s and finding a new audience. Sperry had become a fashion victim, appealing to an older buyer, 90 percent of whom were men.

Which makes it all the more surprising that the once-floundering Sperry Top-Sider is having a high-fashion moment, with everyone from Kanye West to Blake Lively slipping on a pair. In-house designers at Sperry began playing with the look of the shoe, introducing new silhouettes and materials. But the real renaissance began in the late 2000s, when high-profile designers, looking for classic heritage brands, put Top-Siders on the New York runways, playfully transforming a stodgy staple into an edgy fashion statement.

This year, designer Michelle Smith of hip label Milly collaborated with Sperry to create a collection of kicky floral platforms for summer. Japanese streetwear company A Bathing Ape partnered with Sperry on a limited edition shoe last summer that now sells for upward of $400 on eBay. Meanwhile, J.Crew added Sperry to its stores, and the shoe company teamed up with local outerwear company Penfield. Further solidifying its high-fashion status, Sperry recently opened a store on New York’s Fifth Avenue and announced they will start selling accessories like luggage and watches in spring 2013.

“I get the sense that they’ve really come into their own,” says Details magazine fashion market director Matthew Marden. “I think it’s safe to say that Sperry is having a moment.”

But just a few years ago, the company was still looking for an audience. It finally got some much-needed exposure when the California-based label Band of Outsiders approached Reingold and vice president of marketing Karen Pitts in 2008. The label, known for well-made, wearable clothes, has been seen in magazine spreads modeled by young celebs like Joseph Gordon-Levitt, James Marsden, Zooey Deschanel, and Elle Fanning.

Band of Outsiders designer Scott Sternberg came to Sperry Top-Sider needing shoes for his male models at New York Fashion Week.

“At that point they did not have their mojo back,” Sternberg recalls. “But I would always wear Top-Siders myself, and they’ll hate me for saying this, but I would get them for cheap at DSW. I paid $29.99 for them, and I loved them.”

Sternberg says he saw the shoe as a blank canvas, and he promptly started experimenting with new fabrics and silhouettes once he received the green light from the company. An official partnership was born.

“They were great,” Sternberg says. “They sponsored my first show, and we just went from there.”

It was a mutually beneficial relationship. Suddenly Sperry Top-Sider went from discount shoe stores to the pages of GQ. For the high-end Band of Outsiders, Sperry brought Sternberg’s designs to a wider audience at a lower price. Once the Top-Sider flood gates were opened, they were regularly seen on tastemakers like rapper-producer Pharrell Williams.

It’s quite a leap for a shoe company that began in 1935 when Paul Sperry was walking his cocker spaniel on a cold day in Connecticut. He was amazed at his dog’s ability to keep traction on the ice. After studying the grooves on his dog’s feet, he created a shoe with similar treads that would prevent him from slipping when the deck of his boat was wet. It worked.

Eventually the Navy started producing the shoe for sailors, and from there the business was bought and sold a number of times. Sperry is currently owned by Collective Brands, which also owns Saucony, Stride Rite, and Keds.

Reingold arrived in 2001 to start rebuilding the brand. He went about getting the shoes out of bargain stores, and changing the association of the shoe from dated product for weekend loafing to aspirational brand that could be worn year-round. Reingold also expanded into more fashionable women’s styles — Top-Sider heels had arrived.

Today more women are buying the shoes than men, and the average age of the wearer has dropped a good 20 years, according to the company.

It didn’t hurt that preppy style made a comeback in the 2000s, as did the desire for “heritage brands” — American classics that that had fallen out of favor but were being rediscovered by a new generation and suddenly considered cool again. Sperry easily fell into that category.

According to Lisa Birnbach, author of “The Official Preppy Handbook,” and the 2010 follow-up, “True Prep,” the shoe first became popular the late 1970s and early 1980s because it denoted a posh lifestyle.

“You were saying, ‘Hi, I’m Chris, I’m running over to the yacht club.’ But you were saying it with your shoes,” says Birnbach. “Or ‘I’m going to squeeze in a quick sail in between going to the library and going to a cocktail party’ to create this idea of a great life.”

While she helped bring the original brown Top-Siders to the mainstream with her 1980 book, Birnbach is an effusive fan of the brand’s new designer direction.

“The 2012 version of preppy is very different from the 1980s version of preppy,” she says. “We’re seeing a kind of wit exhibited through color and fabrication changes. It’s one thing to have a pair of brown Top-Siders, beat up and maybe taped together. It’s another thing to have a pair of flannel ones designed by Band of Outsiders that have a hipster vibe to them.”

Sperry Top-Sider is planning to build on their profile by introducing sunglasses, belts, swimwear, and small leather goods next year. Reingold says that a clothing line will be introduced “in the next couple years.”

“What I’ve seen time and time again is a more traditional brand try to reinvent itself and change their product into something it’s not,” says Marden from Details magazine. “But they’re doing it just right.”

Christopher Muther can be reached at Follow him on Twitter @Chris_Muther.

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