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Encounters

By ALEX WILLIAMS

“That’s why I’m going to have no teeth,” said Chris Riccobono, the founder of the Untuckit men’s wear label, after a lascivious mouthful of 2013 Joseph Phelps cabernet. “Because it’s four or five days a week where I swirl every sip.”

Demonstrating his tasting technique at a table in the cellar of New York Vintners, a wine shop in TriBeCa, Mr. Riccobono, 38, puffed his cheeks out furiously, like a bullfrog on Adderall, as he sloshed another sip back and forth, back and forth, trying to unearth the subtlest notes of the vintage.

“You look ridiculous, I guess, if people are watching,” he said with a shrug. “But it really changes the flavor profile dramatically.”

Mr. Riccobono knows something about changing profiles. His own had a serious transformation in the past few years, when he went from Jersey guy in a baggy shirt to style avatar.

The change began when he answered an apparently yawning demand among regular guys for shirts cut just so, so that they can be worn with the tails flapping freely over the pants — a look that has become almost universal for the bruhs of the Red Bull generation.

In doing so, Mr. Riccobono, along with his partner, Aaron Sanandres, may have created perhaps the most gloriously literally named clothing company in the history of haberdashery. It makes you wonder why no one has started a baseball cap brand called Backwardzz.

Untuckit, it seems, was an idea so ludicrously obvious that no high-paid marketing genius had bothered to think of it. And fashion insiders sneered when Mr. Riccobono and Mr. Sanandres conceived the company in 2010.

“They said, ‘No, you can’t use that name, it’s not sophisticated,’” Mr. Riccobono said. “‘It should be your name in script or something like that.’ I said: ‘No. The concept is why this is going to be so great.’”

Turbocharged by an infusion of $30 million in venture capital, Untuckit has gone from an e-commerce site shipping out of a spare bedroom in Mr. Riccobono’s apartment in Hoboken, N.J., to a brand worn by high-profile guys like the hockey star Patrick Kane, thanks in part to a steady flow of television commercials on CNN, Fox News and MSNBC.

Two years after opening its first retail shop, in SoHo, Untuckit, which has broadened its line to include shorts, sports jackets, henleys and other staples, is planning to expand to 22 stores nationwide, from nine currently, by the end of this year.

No wonder Mr. Riccobono, a former Providence College tennis player, was ready to raise a glass on a recent afternoon. Tanned and immaculate in crisp AG jeans and a check shirt by — obviously — Untuckit, he was holed up two stories beneath Warren Street in a cavernlike event space lit by Edison bulbs.

The cozy subterranean area at New York Vintners, a boutique wine store and academy of sorts owned by his friend Shane Benson, has been a home away from home for Mr. Riccobono, who ran a popular wine blog called Pardon That Vine before Untuckit swallowed his life. Hunched over a rustic plank table, he popped the cork on an Insignia cabernet, which goes for around $210.

“An amazing vintage,” he said. After sampling it, he called it “a superyoung wine, not drinking to its potential.” His gold Rolex Daytona glistened under the lights as he held his glass aloft and then took another sip. “You can feel that it’s kind of tight.”

The gut punch of this robust California red was a far cry from the 1960 Château Mouton Rothschild Bordeaux that he tried recently, Mr. Riccobono said. A decades-old Bordeaux is complex to the point of being confusing to neophytes. “It doesn’t necessarily taste ‘good,’ it tastes ‘interesting,’” he said.

“Now, the sommelier is going to tell you 58 different things he gets in this,” he added. “‘Graphite. Tobacco.’ Everyone makes fun of that. But with the old ones, you really do. One sip and you’re like, ‘Wow, that really does taste like dirt.’”

Not so long ago Mr. Riccobono was one of those neophytes, in more ways than one. He was little more than an enthusiastic hobbyist when he started his wine blog in 2009. Having just received a master’s degree in business from Columbia University, he was looking for an outlet for his passion during a job search at the height of the Great Recession. And he knew nothing about the apparel business when he dreamed up Untuckit a year later. In both cases, his outsider’s eagerness and Everyman approach were advantages.

“People appreciated me having a hat on backward and an untucked shirt on, talking about wine at a knowledge level that was very high,” he said, “but I wasn’t acting like you had to be super-sophisticated.”

The same proved true with entrepreneurship. “You’re always told that the best idea is the one that solves your problem,” he said. “I used to think, ‘What do I need?’”

The eureka moment occurred on a trip with friends to Las Vegas, when he found himself wearing the same J. Crew oxford, which happened to be a size small, four straight nights, because it was the only shirt that did not look like a tent when worn untucked.

After coming up with a prototype, he called Mr. Sanandres, a friend from business school. “‘I want to throw something by you,’” Mr. Riccobono said. “I had done this 350 times before, where the conversation ends, ‘O.K., I’ll call you next time.’ I just said, ‘Do you ever wear your shirt untucked?’ He goes, ‘I’m in.’”

With $150,000 raised from family and friends, Mr. Riccobono and Mr. Sanandres soon discovered that their simple concept proved complex in the execution. The designers they hired to pattern the shirts, for example, had difficulty wrapping their minds around Mr. Riccobono’s notion of how a shirt must fit and hang in order to look its best untucked.

“No one in the business ever thought much about shirt length,” he said. “It was, ‘Who cares?’ But with Untuckit, shirt length, down to the millimeter, was the whole point. If it’s too long, it’s like any shirt. And if it’s too short, it looks ridiculous.”

Then there were the marketing hurdles. With a limited budget, they were forced to advertise in smaller outlets, like in in-flight magazines, or on the “Boomer & Carton” show on the sports radio station WFAN.

“No one in fashion ever markets on radio,” Mr. Riccobono said. “You can’t see the clothes!”

The guys who were tuning in, however, did not need to see the shirts — which Mr. Riccobono christened with vineyard-friendly names like Muscatel and Sangiovese — to get the concept. Before long, Untuckit was popping up in GQ, and the company was signing the hockey star Brad Richards as a celebrity endorser.

Mr. Riccobono poured another glass of Insignia and swirled it in his goblet.

“Everyone always says, ‘Oh, good legs,’” he said. “‘Legs’ means almost nothing. Smelling the cork means nothing. A great wine like this, you feel it. Seconds later, you still feel it. It’s there. It’s the finish.”

He downed a triumphant gulp, adding, “I always focus on the finish.”