Vineyard Vines: Paradise for Sale

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

vineyard vines

Photograph by David Yellen

According to company lore, a 16-year-old named Shep Murray was skiing in the Alps in 1987 when he came across a comfortable navy-blue quarter-zip shirt. He bought the shirt and, over the years, wore it so often that it got holes in the elbows and rips at the seams. Eventually, Shep stopped washing the shirt, worried that one day he’d pull it from the laundry to find his favorite pullover was nothing but shreds.

By 2004, Shep was co-owner of Vineyard Vines, a booming, to say the least, apparel business dealing in casual wear for casual people. He realized he didn’t need his dirty, holey shirt anymore. He could make his own. That’s how Vineyard Vines’ Shep Shirt—a quarter-zip sweater/sweatshirt hybrid with patchwork shoulders that 13 years later is one of the Connecticut-based brand’s most consistent, and consistently popular, styles—came to be. Just like that—no design genius, no focus groups, no marketing. “I wanted something and I made it,” says Shep, now 46. “Turns out, other people wanted it, too.”

The legend of the Shep Shirt sums up the ethos and entire existence of Vineyard Vines, the company and the brand. There are Shep Shirts for everyone—men, women, kids—and if you own one, you probably own more than one. Like most people, Julia Dzafic, a 32-year-old style blogger in Stamford, Connecticut, remembers her first: thick, cotton, and navy. As does Hannah Gross, a soon-to-be seventh grader in Newburyport who’d seen the shirt on a classmate. “That started our quest,” says her mom, Jill. Each season welcomes a dozen or more new styles of Shep Shirts—variations in color, fabric, pattern, and fit. It is, by all measures, a brand icon. And yet its creation is passed off as a happy accident, a byproduct of a guy who summered in New England and wintered on the slopes just doing what he loved.

Shep and his younger brother, Ian Murray, 42, would have you think everything was this simple. The quick backstory of Vineyard Vines, as they tell it in person and across their various brick-and-mortar and e-commerce platforms: Two brothers, liberal arts grads who’d gone on, as liberal arts grads often do, to become cogs in the Manhattan machine, one day decide they’d rather sell ties than wear them. Shep was 27 and working in advertising at Young & Rubicam. Ian was 23 and doing travel PR at Evins Communications. They quit their 9-to-5 gigs within an hour of each other. “The idea was really a ‘build a better mousetrap’ sort of thing,” says Ian, the lankier and darker-haired of the two, who otherwise share almost identical faces. “We couldn’t find ties that we liked wearing and we figured other people probably couldn’t find ties they liked wearing. So we figured out how to make them and we made them and we sold them.”

Raised in Greenwich, Connecticut, the brothers grew up summering on Martha’s Vineyard and almost instinctively turned to the island’s style for inspiration. They took pictures of the Vineyard’s iconic town signs, scanned them, laid them out, looked up how and where to get silk-printed ties manufactured, and produced 800 of them. They put all the expenses on their credit cards, chose a name that capitalized on the island’s geographic prestige (and was catchy, too), and spent the summer of 1998 on the Vineyard peddling ties out of their Jeep and off their boat. While their friends from Skidmore and Lafayette colleges were going to work at Goldman Sachs and Bear Stearns, Ian says, “the Murray brothers were going around with a Tupperware full of ties…. You had to swallow your pride a lot.” (Still: Their cubicle was a boat.)

At first they heard a lot of nos. People on Martha’s Vineyard and along the coast, Shep says, had never seen a $65 tie. “They’d only seen polyester ties,” he says. “I remember going into John Farley Clothiers in Newburyport in the fall of 1998 saying, ‘We’ve made ties.’ The owner said, ‘Tie sales are terrible!’ And I said, ‘Our ties don’t look like yours,’ which were brown and black and gold. He said, ‘No, tie sales are terrible!’”

Still, they received instantaneous positive feedback from their friends, and to Ian and Shep, that was the demographic that mattered. The original four styles—the town signs, bluefish, Jeeps, and a pattern featuring the outline of Martha’s Vineyard—were soon followed by more of the same: sailboats and golf clubs and cheeseburgers and pool floats. They made the prints small so that from a distance, the ties appeared more conservative than they really were, an inside joke for the wearer and his friends: I may look like I’m conforming to the expectation of adulthood, but really, I’m wearing a tie decorated with a hundred tiny margaritas. The idea, Shep says, was “to help people bring the good life to work with them. How do you tell people that you love sailing or golf or the Kentucky Derby? How do you tell people that instead of the office you would rather be in a place with palm trees?”

vineyard vines

Beyond the Whale: Clockwise from left, Vineyard Vines ties in a variety of cheerful patterns; the company creates custom clothing collections for prep-friendly events such as the America’s Cup yacht race; the classic Shep Shirt is one of the brand’s most popular styles. / Photographs by Lizzy Barrett, styling by Tommy White

Within three years they’d passed the $1 million mark in sales. Today, Vineyard Vines remains privately owned, and even as such industry stalwarts as Brooks Brothers, Ralph Lauren, and J.Crew face shrinking revenues and store closings, Vineyard Vines keeps growing, with about 100 locations across the country, up from 70 a year ago. The brothers won’t release figures, but in 2016, Reuters estimated the company’s value at nearly a billion dollars. In Vineyard Vines’ new 91,040-square-foot Stamford, Connecticut, headquarters, which Bloomberg described, probably not inaccurately, as “the preppiest office in America,” each of the building’s four floors is themed to represent a different beach destination. It overlooks a marina where each brother keeps a boat, though neither boat is there the day I visit in late spring. “Where’s my boat?” Shep asks an assistant sitting at a desk outside the single office he and Ian share. She doesn’t know. He also keeps boats in Key Largo and “a few other places,” he says. They are all named Vineyard Vines.

Of course, ties alone did not buy those boats, or this building. Nor did the clothes that Vineyard Vines eventually sold. What did: selling people their very own slice of the good life, or the promise of it; selling the brothers’ “quit your job and follow your dreams” story; selling the tale of the Shep Shirt and many other stories like it. “Everybody, when we started, said we couldn’t do it,” Shep says. “We were two cans versus a world of can’ts.”

But while the Murrays have undoubtedly had some very good days, and made themselves very rich, by providing colorful, feel-good clothes to people who want to feel good, in doing so they’ve also upended an entire style—and engendered a fair share of criticism. Prep, a staple of New England’s old-money families, was traditionally a staid-by-nature aesthetic characterized by stiff navy blazers and passed-down penny loafers. Now, thanks to Shep and Ian Murray, overseers of modern prep’s most dominant brand, it might be best described as a Jimmy Buffett concert gone to work—but cutting out early, bro!—pink whale koozies in hand.

Alternately beloved by millions and chided as a fashion copycat that caters to and even spreads a watered-down form of elitism, Vineyard Vines has taken a stodgy, snobby, century-old cornerstone of New England life to the masses in a new and accessible way. It’s also left fashion observers dumbfounded, wondering how the hell they did it.

The answer? For one thing, it’s not exactly fashion they’re selling.


A Preppy Timeline

The preppy style has been an entrée to the better life since as far back as the late 1940s, when FDR’s post–World War II G.I. Bill gave college scholarships to vets, many of them lower- and middle-class boys who landed at Ivy League universities with prep school kids and wanted to look like they belonged. Corporate culture was the vehicle for growth in postwar America, and you dressed for the life you wanted to have. “In those days, everyone wore a suit and tie to work, to church, to baseball games, no matter who you were or how much money you had,” says Richard Press, whose grandfather founded men’s clothier J. Press in 1902 on the campus of Yale. “Young people wore a suit and tie to the nightclubs.” Even the more casual styles followed a rigid format: thick wool fisherman sweaters, tweed jackets, and all-cotton button-downs, not a technical fabric in sight. While weekend wear existed, Press says, its place was at the country club or on trips to Bermuda. “When you’re vacationing in Newport or Marblehead or Kennebunkport, are you going to wear jeans and some lousy tee? No. You have class aspirations, and that won’t work,” he says.

For years, Brooks Brothers, in business since 1818, held the urban market and J. Press the campus one; family-owned local stores, such as the Andover Shop, in Andover (and later Cambridge), and Richards, in Greenwich, brought the style to small towns with the right clientele. “The look was sober and discreet,” says Christian Chensvold, the founder and editor in chief of the website Ivy Style. “It was subtle.” Wearing it bestowed a sense of empowerment, security, class, and taste, even if you had none of the above. Using the word “prep” to describe this manner of dressing didn’t actually come around until 1980, when recent Brown University graduate Lisa Birnbach released The Official Preppy Handbook, a satirical guide to the post–prep school set and all their habits and habitats. But the clothing Birnbach described hadn’t changed much in decades.

There were nuances, though, and they mattered: The “right” Nantucket Reds were bought at Murray’s Toggery Shop, on Nantucket, where the style of pants had originated; the only acceptable madras was the hand-loomed bleeding kind in which the colors ran together in the wash, a defect flipped to confer status. Still, the snob factor lessened over time as faster fashion took hold. In the late ’60s, Ralph Lauren brought Ivy style into the mainstream and into department stores, followed by J.McLaughlin in 1977 and J.Crew in 1983. The late ’80s saw the height of popularity for European imports such as Fred Perry. And who could forget the little green alligator made famous by Lacoste? Then came the mall brands: Tommy Hilfiger, Abercrombie & Fitch, and American Eagle. Manufacturing went overseas. Status was transferred to the label and away from the notion of authenticity. Quality went down, but that was okay: More people could afford the clothes and join the clique.

One reason prep has retained its appeal for more than a century is that it offers something nearly everyone wants: the ability to convey a nice life. Even before apparel companies began repositioning themselves as “lifestyle brands,” prep was always about selling an aspiration, a pass into an exclusive club. People were drawn to the elitism if it meant they could be part of it.

These days, of course, the suit and tie is a rare breed, reserved largely for those who work in ultra-traditional professions—bankers, lawyers, detectives, at least on TV—or who are ultra-traditional themselves. Today’s American dream, however, is about running away from corporate life (though not corporate cash). Shep and Ian, for example, don’t wear ties unless forced to. (“I had to wear a blazer on Saturday night with my wife,” Shep says. “It was just terrible.”) When it comes to quality, meanwhile, most customers don’t care, so long as the price is right and it makes them look and feel a certain way. “You can’t even find bleeding madras anymore,” Press says. And while some still travel to Murray’s Toggery for Nantucket Reds (or, more likely, order them online), the mainstream consumer is more likely to buy his reds from the brand that fits the best, is the cheapest, and is right there in front of him.

That’s where Vineyard Vines came in. What they were doing when they started wasn’t particularly revolutionary—we’re still talking about ties—but the open invitation to join the club was something novel. The lifestyle they were selling was different, too, and timely, reflecting a shift in focus from how you made your money to what you did when it came time to spend it. “They were able to tap into something archetypal that is a very mainstream, middle-class version of a sort of New England lifestyle,” Chensvold says. Vineyard Vines is, no doubt, a mall brand, but also a Main Street one. “I think it’s easy for purists to mock them, but prep is something that constantly renews itself.” Vineyard Vines, Chensvold explains, is staying true to the style, albeit in a diluted way, “with their madras-y shirts and belts and models wearing boat shoes,” while in other ways playing to general consumer tastes—most poignantly, he says, “to a consumer who doesn’t know the difference.” Or as Press puts it, “Is Vineyard Vines a little copycat? Absolutely. But certainly not the first.”