The brothers admit they knew little about what they were doing. Over the years, they've had all kinds of fabrication and distribution mishaps, but they were lucky to hit upon a product that was easy to sell—ties take up little space, are one-size-fits-all, and have a high profit margin. The brothers' best asset was being able to project what their customers wanted, figuring if they liked an activity or a style, other men would too.
They relied on these insights as they expanded into sportswear. "I have a dozen pairs of these exact pants," says Shep. "For most guys, it's just easy for them to wear the same thing—they wear a suit or whatever during the week, then they come home on the weekends and change into khakis or jeans," he adds. "We have shorts in about 12 colors. Guys will buy 10 pairs of khaki shorts and then one or two in colors."
The company has inevitably been labeled "preppy"—The Official Preppy Handbook editor Lisa Birnbach devoted an entire page to it in her recent book, True Prep: It's a Whole New Old World—and with all of the white, navy, and pink décor around the office, it's not hard to see why. But the two brothers shrug off the categorization. "I don't think preppy is a fashion; it's more a way of life," says Shep. "Take what we are wearing right now—if we walked in 25 years ago or 25 years from now, this would still be a fine shirt."
The company makes versions of its shirts with a whale icon on the breast, the breast pocket, the hem—or nowhere, depending on whether the wearer wants a visible association with the brand. "Our guy never tries too hard to impress. Our clothes aren't supposed to impress; they're supposed to help him live a nice life," Shep says. In other words, the clothes channel the spirit of the Vineyard itself, where the coolest guy is the one with the most beat-up Jeep, no matter how many millions he might have invested in his oceanside spread.
Expanding into clothing sparked the first friction between the brothers over their vision for the company. "Shep's perspective is very classic, old-school Palm Beach, faded Nanucket reds, and my perspective can be a little more towards fraternity house, what the guy is wearing on the dock," says Ian. As they've worked out the kinks, how- ever, they've realized that the unique style of the brand owes as much to the fusion of those two attitudes as to either one on its own. Shep has recently focused more closely on details of style and fit, as well as classic items like woven shirts, while Ian has gravitated toward swimsuits, outerwear, and shaping the overall image of the brand.
As the company has increased its number of stores, it has focused on offering more specialty items such as holiday ties or special patchwork patterns to keep customers making purchases beyond the basics. For example, for the Kentucky Derby collection, the company went beyond horse motifs and created ties with mint julep icons and dresses and jackets with elaborate patchworks made of jockey-silk patterns.
The Murrays' own version of the good life may have changed in the past 14 years, from beers on the dock to cold cuts on the family picnic table. But their desire to transmit the philosophy—that life is too short not to enjoy—hasn't. "Your good day is different from my good day, and when we build a store or put out an ad, we try and live up to that," says Shep. Even if, occasionally, they have to put on a tie to do it.
