No Country Club for Old Men

Despite being remembered for acid-washed denim, leg warmers, and spandex, the 1980s offered one lasting fashion trend: the ubiquitous polo shirt. The decade saw an arms race among such polo powers as the alligator (Lacoste), the laurel (Fred Perry), the pony (Ralph Lauren), and the pot leaf. Well, technically it was a Japanese maple that adorned the breast of the cult-favorite, nearly-forgotten über-prep brand Boast. The company retired the look in the early '90s but is now bringing it back under the leadership of two former devotees, who offer proof the logo does not depict a controlled substance. "The pot leaf has extra petals," says John Dowling, the brand's co-CEO. "It has longer petals, it's more serrated. It's a different thing."

Japanese maple it is, and Japanese maple it has been since 1973, when a Greenwich (Conn.) tennis pro named Bill St. John founded Boast and drove from country club to country club selling the shirts out of his station wagon. The insignia actually grew out of the company's earliest days, when St. John purchased material for his shirts from a Japanese kimono maker that used the leaf in its designs. Regardless, the story of the company's unusual birth and iconography became cocktail hour fodder in Darien and Southampton, and it wasn't long before Boast—named after a squash shot that hits the side wall before the main wall—became de rigueur statement apparel for the slightly irreverent members of the Andover set, George W. Bush among them. At its mid-'80s peak, when it could even be found in the wardrobes of eminences such as John Updike, the company employed 35 people and raked in a modest $8 million in annual sales. However, St. John decided to pull it from the commercial marketplace in the early '90s to focus on selling exclusively to country clubs, which place sizable orders of blank white shirts onto which they sew their own logos. In the past decade, Boast quietly maintained about 1,500 such accounts. After purchasing the trademark from St. John last year, Dowling and his partner, Alexander Tiger, both 38, have put aside their respective careers as documentary filmmaker and corporate lawyer to revive the brand for a new generation of irreverent prepsters.

Dowling and Tiger are, in one sense, perfect for the gig: They look preppy, but not in that obnoxious Ricky Schroder sort of way. The two met through "mutual prep school friends," as Dowling says, when he was attending Groton and Tiger was at St. Paul's. From there, Dowling went to Harvard, and Tiger to Princeton. "We've got all our bases covered," Tiger says half-jokingly. Dowling looks down and shakes his head. "That's just so obnoxious-sounding," he says. "Yeah, I know," Tiger says. "Don't say that."

Tiger got the idea to relaunch Boast three years ago when he was looking through his closet. "I had old Boast shirts that were so worn out. I thought, 'Where did this brand go?' " Soon, he began contacting St. John to strike a deal. He and Dowling were not, St. John says, the first upstarts eager to reintroduce the shirts. However, Tiger deployed true WASP charm—he sent St. John's assistant bottles of wine—and a shrewd business strategy: begging. "I said to his assistant, 'Put this letter in front of Bill. Make him read this so he understands we're huge fans of Boast and loved it growing up.' " After six months of pestering, St. John finally picked up the phone.

In late 2007, Tiger flew to St. John's Palm Beach (Fla.) home to try to seal the deal. As to be expected among gentlemen, the Boast founder insisted they first play some tennis. "Bill was an All-American at Cornell. I think he liked Alex because he plays really well," Dowling says. "That separated Alex from the usual private equity types that were calling him every year." St. John, who remains a consultant to the brand, more or less agrees with that assessment. "Everything that had to feel good in order for me to accept a partnership felt good," St. John says. "Our skills are complementary, and they have the right passion for the brand. I never wanted to be absorbed by an existing apparel company."

Tiger and Dowling subsequently raised "under $1 million" for this fall's relaunch and quickly learned that Boast had many fans, including branding guru Andy Spade, the Kate Spade and Jack Spade co-founder. Spade agreed to consult on design, branding, and product rollouts. "I think people want something with some realness to it. Hollister is made up," he says. "St. John was one man trying to do something the Europeans were into. The guy's story is so good." So is Spade's. "Anything Spade dips into, I think, is going to do great," says Tim Bess, an analyst at Doneger Group, a trend forecasting firm. "Boast will do well. It will get a buzz."

So far, Boast sells three styles of $68 polo shirts and one $1,200 blazer on its website, which could easily pass as Royal Tenenbaum's vacation album. They're also working on a "really nice-fitting" women's polo for spring 2011. Children's wear could come after that, and Spade hopes to introduce a tie-dyed style. The timing couldn't be better: Heritage brands such as Pendleton, Levi's, and Stetson have exploded in the past few years. "The fact they decided to launch with the polo is interesting," says Bess. "I think that could work for next year."

Boast orders have come in from over 20 states so far, from New England to less logical places such as Wyoming, and Dowling and Tiger hope to be selling through specialty retailers, and at upscale boutiques, within six months. It's a "slow-build" strategy, says Spade. "A lot of kids don't want to buy big brands that are pushed on them. Find us, we're here, and we're going to do well." Of course, the Japanese maple leaf doesn't hurt.

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