Neckties from the 2012 Kentucky Derby collection
In reality, the Murray children were exposed to excitement year-round; their parents were writers for Robb Report and took them to Europe, Africa, and the Caribbean at a young age. The brothers absorbed the lessons of customer service without even knowing it—seeing how places could be enhanced or spoiled by the abilities or weaknesses of the people who ran them. "Staying at a property is not about it being a nice property," says Shep. "It's all the things that go along with it—the people make a brand come to life."
The idea that people make the brand informs much of Vineyard Vines' marketing strategy. Instead of only using professional models in their catalogs, the brothers cull stylish men and women from the Vineyard Vines staff, or friends whose personal style exudes the sporty-summery "good life" approach to dressing. Ian pages through a catalog, pointing out the man who drives their launch in Edgartown, and a grizzled member of Jimmy Buffett's band fishing in the surf with white hair and a tan. "Any guy sitting at his desk in Midtown looking at him is going to say, ‘What's wrong with my life?'"
The brothers should know—they used to be those guys dreaming of breaking free of the corporate world. Despite their father's warning not to be in a hurry to put on a suit after college, both brothers landed desk jobs in New York in the late 1990s. "We'd find ourselves on the train platform in the morning wearing these suits, feeling miserable, and staring at other guys who seemed miserable and who looked like they had been doing it their whole lives," says Ian.
Searching for an exit strategy, Shep and Ian came up with the unlikely notion of selling neckties. For Christmas, Shep had received a tie from his mother with icons of Nantucket created by a local artist. "The idea was so cool, but the execution wasn't," he says. "It was done on poor-quality fabric, and the scale of the icons was too large." Still, he thought, if the average executive couldn't be flyfishing on a Monday, "Wouldn't it be great for people to bring the Vineyard to work with them?" Most neckties sold on the Vineyard were polyester club ties, priced around $20—fitting with the Vineyard's reputation for understatement and reverse snobbery. But the Murrays sensed that summer islanders would opt for something of better quality for their workday attire once they returned home.
Both brothers quit their jobs and maxed out their credit cards, taking a page from the entrepreneurs on the next island over who had pioneered Nantucket Nectars by selling juice to boats in the harbor from their launch. While Shep stayed in the city making designs—Vineyard street signs, an island silhouette, and a whale as an homage to their father's carvings—Ian drove around the island taking orders out of the back of his Jeep. The day before the company was officially to start selling, July 4, 1998, Ian had already presold $1,800 worth of ties. "That's when I realized this could work," he says.
