Vineyard Vines: Paradise for Sale

How two manhattan suits stole the soul of New England and turned the brand into a billion-dollar empire.


Shep and Ian are not, by their own admission, “fashion guys.”

“We never claimed to be and I don’t think we ever will be,” Ian says, dressed in khaki shorts, a plaid button-down, and a black fleece vest, which is likely the same outfit he wore 20 years ago as an undergrad, except now it’s all Vineyard Vines.

“Speak for yourself,” Shep interrupts. He’s being funny; he dresses in shorts and Crocs every day, all year long. That blazer he wore a few nights back? It was bearable only because it had some stretch. “It performs like a sweatsuit,” he says.

Back when they were working in Manhattan, Ian had a single Brooks Brothers suit that he bought at an outlet and wore every day for the nine months he slogged to an office. Sometimes he’d borrow one of Shep’s fancy ties—Ferragamo or Hermès—“and if I wore one of those, people would tell me, ‘I like your outfit today,’ and if I wore something else they wouldn’t say anything,” he says. “People judge most books by their cover as much as they say they don’t.”

The brothers make an effort to downplay their privileged upbringing. Their parents were freelance travel writers; there was no trust fund. “We grew up on a writer’s salary,” Ian says. Still, they were no strangers to the good life. They went to the same private school their sons currently attend, and summered, of course, on the Vineyard. Every year their grandmother, a well-known Manhattan literary agent, flew the extended family to Club Med, where the guys learned that “it was the people who made everything come to life,” Shep says. Anyone can build a pretty store. “We’re really in the hospitality business,” he adds.

They knew this from the very beginning, when they first positioned themselves, and authentically so, as guys that Wall Streeters could identify with: work-to-live types who’d gone straight from wearing the jeans-and-fleece uniform of the Ivy League or NESCAC to working office jobs for the money, and often very good money, but whose hearts were back home in Hingham, Marblehead, or Newport. Guys who, like the Murrays, didn’t really want to wear a tie every day, either. The late ’90s was also the heyday of tech startups, Ian says, “and every office had a climbing wall and a Ping-Pong table.” While a lot of those 9-to-5ers didn’t actually have to wear ties, when they did, like “for a wedding or a graduation, some special thing,” Ian says, “they welcomed a way to have some fun with it.”

Printed ties were hardly novel in preppy style, nor were bright colors. Yet there was an etiquette to both that Vineyard Vines ignored, designing patterns that often bordered on corny—or were even undeniably so, depending on how you feel about a nice beer-and-lime print—though the small size made them subtle enough for nearly any occasion. It was how finance boys did outré. The bright colors, meanwhile, “made it easy for boring bankers who’d wear a blue or gray suit most days to close their eyes and pick a tie that both popped and carried a certain amount of class,” Chensvold says. “This was a guy who didn’t grow up on the subtleties of Ivy style, of course, but maybe one who went to a Northeast school, joined a frat, and got into banking or law.”

There was just as much appeal in the aspirational story the Murrays were selling, and like other great marketers, the brothers did a whale of a job getting their message out there, combining commerce and content before “brand strategist” was even a job title. One day in 1998, Bill Clinton was “on island,” as locals put it, when the story broke that he had testified in the Monica Lewinsky case while wearing a tie Lewinsky had given him. Ian hopped on his bike and hightailed it over to the Edgartown elementary school, Clinton’s island press HQ, where he stood around for hours with a bunch of ties draped around his neck. “I’m a local businessman and we have a necktie business,” he told the news crews that had assembled. “We’re here because we understand that President Clinton is wearing ties that young people are giving to him, so we wanted to see if he’d be interested in wearing one of the ties we’ve made.” He didn’t deliver one to Clinton, but he did get his photo, and the Vineyard Vines name, on the 6 o’clock news. “We learned the power of the press,” Ian says, and “how it’s free if you’ve got a story to tell.”

Slim budgets in the early days led to lasting brand decisions. The brothers photographed friends for their early catalogs and have remained committed to using everyday people as models ever since. Years later, their ties appeared on celebrities and on both sides of the political aisle—John Kerry wore a lacrosse print on the cover of Newsweek; Rudy Giuliani favored the American flag. For years, visitors to the White House would get a tote bag with a Vineyard Vines tie bearing the presidential seal. (Shep says the Trump administration is the first in a while they’ve stayed away from. “Too ugly a time for America, no matter who you voted for,” Ian explains.)

The company jumped from ties to clothes by 2004, after a business associate brought them a pair of boxer shorts re-created in one of their prints. It was time, they decided, to go beyond helping people bring the good life to work and instead help them dress for the good life they had (or wanted to have) outside of work. Weekend wear for men and women at first, and later for kids—polo shirts, bathing suits, fleece vests, and more—followed the same colorful, irreverent format that appealed to people who found high fashion intimidating. Which, it turns out, are most people. They created a logo—a smiling pink whale in homage to their dad, who had carved whales as a hobby—expanded their presence in department and specialty stores, and began toying with the idea of establishing freestanding Vineyard Vines boutiques that would carry the brand’s entire line in one place. Revenues tripled from 2004 to 2007 and have grown year over year ever since.

The creation of the logo, which appears most prominently on shirts, à la the Lacoste alligator, played no small part in the company’s success. Ian says he’ll see the brand’s smiling whale sticker on cars “that typically aren’t the sort of cars to have bumper stickers.” Hannah, the soon-to-be seventh grader in Newburyport, concurs. “The whale is really cool,” she says. “If it didn’t have the whale as a logo, I wouldn’t wear it.” (She and her friends also collect Vineyard Vines seasonal stickers to decorate their school binders and trunks for sleep-away camp.) When my 12-year-old stepson, who’d just as soon wear the same sweatshirt every day, reports that lots of kids at his middle school wear Vineyard Vines and I ask how he knows, he tells me it’s because of the pink whale. This is a person who may not notice if he’s wearing his own shirt inside out.

Custom has also been a big part of the business, and over the years the brothers have partnered with colleges, sports teams, and prep-friendly events such as the Kentucky Derby and the America’s Cup yacht race to not only sponsor events but also create clothing collections to sell in conjunction with them. Pieces from this year’s America’s Cup Collection include swim trunks, T-shirts, gingham button-downs, and a navy blazer embroidered with the America’s Cup crest that sells for $595. A pop-up store launched at J.P. Morgan Chase’s Wall Street location last summer featured Vineyard Vines ties branded with the bank’s blue octagon logo. Somehow, this does not alienate the legions of middle school and young-adult fans the brand has accrued, nor the style-blogger set. A stroll through Instagram reveals that most of the brand’s zealots—some paid “influencers,” many just regular people—are in their teens through their thirties, living what look to be very good lives, indeed. (A search for “#vineyardvines” turns up “related” hashtags that include, in order, #wineoclock, #morewineplease, and #winenot.) Shep refers to the company tag line often: Every day should feel this good. “That line, it just resonates with people,” he says. “Your idea of a great weekend is different from mine. But hopefully our clothes help take you there,” whoever you are.


What you wear is no longer just a form of expression; it’s also a definition. Many people wear Vineyard Vines because they like the colors or prints that make their clothes feel personal. But just as many, if not more, wear it because it says something about them. Prep has always been centered on conveying, through your clothes, that you have money or privilege or class, but mostly money. And while prep, as a style, goes in and out of fashion, one of its appeals is that the clothing remains constant: the crew-neck sweaters, pearls, and collared shirts endure from one generation to the next.

Vineyard Vines plays on that and works much the same way. Styles progress but rarely deviate from those established nearly 15 years ago. “What my husband and I like about it is that it’s so easy,” style blogger Julia Dzafic says. “Neither of us is that fancy. It evolves but it’s never about the latest trends. It’s always the same.” In that sense, Vineyard Vines remains true to the New England sensibility: People want to buy something that won’t go out of style in a few months, even if that means buying something that’s not, in fact, in style at all.

This is why Vineyard Vines has been immune to the ebbs and flows of trendiness; Chensvold describes it as an “anti-trend brand. They’re certainly not doing anything avant-garde.” But even if the brand dances on the grave of true prep, its success is based in large part on a quality that’s entirely in line with the prep sensibility: undeniable multigenerational appeal. While it would seem nearly impossible to design clothes that both a 14-year-old and his 44-year-old dad would want to wear, that’s exactly what they’ve managed to do. “In Connecticut,” Dzafic says, “all the bankers go to work on the train commute wearing a fleece vest and Vineyard Vines shirt.” She also reports that the closest Vineyard Vines store to her, the one in Greenwich, is always packed with teenagers. Her six-year-old half-brother is a fanatic: “He has the stickers and, like, 1,000 bow ties.” So, by the way, is her dad. And that’s classic prep: “For 80 years, that’s been the saying about Ivy style,” Chensvold says. “It gives a young man dignity and an old man youth.”

Criticisms have included that it’s a brand for people who ask other people where they summer, but to the millions of Vineyard Vines fans—some of whom have summer places but many of whom don’t—that’s precisely why they buy it. “It makes you feel like summer year round,” Dzafic says. And, bright colors or not, it’s become the safe option. For a whole lot of people, Vineyard Vines is a style to buy into when you don’t know what your style is; it’s a way to look different and unique while also having the safety of looking like plenty of others. Vineyard Vines may not be “the right” way to dress for a prep traditionalist or, on the flip side, anyone interested in fashion trends, but empires aren’t built on individual tastes. After all, looking like you belong is what prep—and, in turn, retail dominance—is really all about. And Ian and Shep know full well you can’t get any more Vineyard than that.