Shep and Ian Murray, on the shore of their beloved Vineyard

"Ties are, like, these horrible things," blurts Shep Murray, cofounder and CEO along with his brother Ian, of Vineyard Vines, the cult clothing company that got its start selling—and is still best known for—neckties. The brothers have often said, "We make ties so we don't have to wear them." For them, it's more than an offhand statement. Case in point: For an event in Manhattan to benefit the US Sailing Team, Shep says he needed "to buy a tie at the store. Because the reality is I only have one or two."

As we speak the Murrays are slumped into the cushions of their office's beach cottage furniture; the rattan chair and bulky blue-and-white couch might seem more at home in a Vineyard sunroom than in Stamford, Connecticut, where their corporate headquarters is located. You could say the same thing for the brothers themselves, who are wearing near-identical outfits of vests, khaki pants, and checkered shirts—purple for Ian and green, blue, and pink for Shep—and look ready to leave the office for the deck of a 40-footer, or at least a few dark and stormies on the dock.

You're not likely to hear many case studies at the Harvard B School where owners express such ambivalence about their company's core product. And yet, the Murrays have turned their tongue-in-cheek tentativeness into a marketing strength, perhaps by tapping into a key male truth: Most men hate wearing ties and would rather be anywhere but behind a desk.

The first Vineyard Vines store, in Edgartown

Vineyard Vines has triumphed precisely by playing into that sense of wish-fulfillment with an array of high-quality neck-chokers featuring whimsical nods to what the brothers refer to as "the good life." The most straightforward patterns feature icons such as sailboats, tennis racquets, and the company's signature whales, a symbol of its origins on Martha's Vineyard, in shades of lime, pale yellow, and pastel pink—the same hues that color Oak Bluffs' gingerbread cottages. The zanier patterns involve gentle visual puns like slices of lime interspersed with keys ("key lime") or golf clubs stuck into sandwiches ("club sandwich").

The high quality of the material and the waggish artfulness of the designs keeps them more cool than kitsch. The ties have been worn by every living president and quite a few candidates (John Kerry is a fan of the lacrosse tie), as well as New York Mayors Rudy Giuliani and Michael Bloomberg and financier Warren Buffett (who wore their bull market tie on the cover of the Forbes 400 issue). Last year the company set a target of $100 million in sales, which represents almost a doubling from five years ago, a result of their expansion in 2005 from ties to a complete clothing line for men, women, and children. In the past year and a half, the company has doubled the number of stores to 20, including new locations as near as Hingham, Oak Bluffs, and Logan Airport and as far away as Plano, Texas, and Newport Beach, California. The Murrays have also signed licensing deals with the NFL, NHL, and MLB, and Vineyard Vines' clothing is the "official style" of the Kentucky Derby.

As much as they've sold clothing on the basis of quality, whimsy, and style, the brothers sell something else as effectively—themselves. Or rather, their personalities, which have earned the brand a word-of-mouth following. "Ties are not cool," says Ian. "It wasn't what we were selling that was fun, it was how we did it. We love to play guitar, we love boats, so we said, Let's sell as if we are promoting a band or a boat-building company and create energy and excitement around this really boring product." The two brothers clearly get along well, sharing an office and frequently interrupting to finish each other's sentence. As befits an older brother, Shep, 41, is bigger and more outspoken, while Ian, 37, is quieter and more introspective. But both share passions for boats, music, and drinks on the dock.

The Murrays grew up in Greenwich, Connecticut, just five miles from where their headquarters is now located. Shep grabs a black-and-white photo of their old house and points to a wooden carving of a whale made by their father, Stanley, on Martha's Vineyard. Stanley Murray went to the Vineyard every year as a child, and carried on the tradition with his own family. "We always said we spent nine months of our year waiting for three months to live," says Shep.