On the spectrum of Nantucket status-signifiers—with casually mentioning Surfside Beach on the acceptable end and plastering big ACK stickers all over your Volvo on the other—wearing a pair of Nantucket red pants probably falls somewhere in the middle. In other words, those who have been to Murray's Toggery Shop will understand, but if you have to ask, well, you probably won't be making an appearance at the Kerry–Heinz July Fourth clambake.

Nestled at the top of cobblestoned Main Street, Murray's has been dressing WASPS in the uniforms of leisure—obnoxiously hued, sportily durable, and maybe a bit silly—since 1945. The first pair of Reds appeared around 1960, when Philip Murray inherited the store from his father and remade Brittany trousers (named for the sail color on boats in the Brittany region of France) using a new dye hat, with a bit of sun and salt, paled to just the right shade of pink. Men started wearing them on the water, at cocktail parties, and before long, to that most sacred ritual of the Preppius inebriates species: weddings. Today, Murray's sells as many as 6,000 pairs annually. "People liked the pants because they held up when they went sailing, they weren't too expensive, and the heavy cotton canvas faded, " says Philip's daughter Trish Murray-Bridier, who has kept the store in the family by managing it with her husband and brother. "Nantucket Reds remind you of your vacation."

As Murray's has grown over the years into an 8,000-square-foot space and opened a branch on Martha's Vineyard, its stock has broadened to everything from blazers to madras bathrobes to Truefitt & Hill shaving products—and every grosgrain belt and lighthouse-embossed necktie in between. But unlike other pantheons of prep such as, say, the Polo Mansio, the Murray's retail experience is refreshingly light on yessir ministrations. Instead, staffers are on a first-name basis with the old guarders (Nelson Doubleday, Dick Gamble) and the new (Tommy Hilfiger) who toddle in—and just a few months ago, George H.W. Bush personally called in an order of Reds for his daughter Doro.

Phoning it in from Kennebunkport is convenient, but an hour on the premises will reveal items you never ever knew you wanted until you saw them (an over-the-shoulder tote that stows 10 bottles of wine—husbands, lock up your wives) as well as items probably better suited to a Yale secret society (a skull and crossbones needlepoint cummerbund). The Reds alone take up the entire back wall, and in recent years the collection has expanded to shorts, hats, sweaters, and—que scandale!—yarmulkes. "Personally, I don't love seeing Reds top to bottom," says Murray-Bridier. "I like the contrast. But there are some people who wear the pants with the socks, the shirt, and the sweater, and they buy it that way. And even some husbands and wives who want to dress alike." She widens her eyes and arches her eyebrows, as if to say, "Yikes." Even the Murrays, it seems, have their limits.