Man from UNTUCKit

cartoon illustration of men walking into an "UNTUCKit" machine
Mark Steele

There once was a man in Hoboken
With shirttails so long he could stroke ’em
He said, “What a slob —
Their lengths I must bob
So my bad untucked self will look smokin’.”

— Anonymous


A crisis of confidence gripped the metro area. In front of his full-length bedroom mirror Today’s Man trembled inwardly with self-doubt as he tossed his eye over his shoulder to study the effect of his liberated shirttails. He had seen, now and again, in steakhouses and wine bars, what was clearly a more capable, more favored member of the species wearing his shirt outside his pants at an effortlessly perfect length and fit, implying taste, confidence, brashness — a mysterious piece of luck, that shirt, or else a marvel of custom tailoring, because Today’s Man, no matter how hard he looked (not that he had time to look, busy as he was), could never attain this ideal for himself. So he settled, accepted his lot, untucked himself at his peril, suppressed his anxieties, even convinced himself that he was bringing it off, never guessing that his fiancée, more than once, had confided to her friends her embarrassment at his appearance, comparing him in his long, unfurled shirt-flaps to a ten-year-old boy or a happy-hour schlub. 

Enter, then, like a genie uncorked from a 2004 Barolo at a back table at Delmonico’s, Chris Riccobono ’07BUS, wine-tasting maverick, Knicks fanatic, and hellraiser of business casual, an idea-spouting risk taker who, in his resolve to fashion his life to his own personal specs, has located entrepreneurism’s Holy Grail: a gap in the marketplace. 

“I’m one of those guys who is always thinking of anything that can go,” says Riccobono, standing by a rack of men’s shirts in a showroom on West 20th Street. Not everything goes. There was his niche-market online dating service idea called Love for Little People ( and a reality-show pitch titled Cabin Fever, in which contestants on a two-week cruise vie to become Hollywood agents, and are judged by people they think are influential agents but who are in fact impostors — a cab driver, a janitor, a homeless person, and the like. No, not everything goes, but Riccobono’s latest shot has the look and feel of inevitability, and certainly of cotton: the Bergen County, New Jersey, native has created, you might say, a new jersey. 

“I had forty shirts, and there’s only one that I could wear untucked,” Riccobono explains. “I wore it everywhere. It was a J.Crew, a small — keep in mind, I wear a large. I talked to my friends, and they had the same problem: they had beautiful shirts but couldn’t wear them out because they were too long.” Riccobono’s idea, which he christened UNTUCKit, was a button-down shirt whose lower hem hung past the belt line at the optimum, market-researched length of midfly. 

“I don’t like being in a suit, I don’t like being shaved, I don’t like uptightness,” Riccobono says, sounding more Occupy than Wall Street, though in his John Varvatos boots, Seven jeans, and dark-blue Ted Baker jacket over an UNTUCKit “Paso Robles” red plaid shirt, he doesn’t appear bound for Zuccotti Park. Whether it’s wine racks or clothing racks, Riccobono’s focus is fineness: he pulls out a pink and navy checked shirt (appellation: “Chablis”) made from 120-thread two-ply Egyptian cotton, holds it up to express its lightness, its breathiness, and urges Today’s Man to “get away from the uptightness of life, untuck yourself, and still look sophisticated.”

This from a finance major who, in May 2001, came out swinging from Providence College, where he’d gone to play Big East tennis, ready to trade his racket for a jacket in Lower Manhattan, even if it meant keeping his shirt in his pants. “I never wanted to go the corporate path, no matter what,” he says. “I saw finance as a bridge to doing something on my own: you need money to start a business.”

His plans for Wall Street were altered that September when the attack on the Twin Towers turned the financial district into a toxic disaster area. Riccobono recalibrated. He was accepted into General Electric’s technical-sales and leadership program to learn about medical sales, a starting rung on the corporate ladder. During his training sojourns in Miami and Milwaukee, he studied for his GMATs, and in 2006 he entered Columbia’s Executive MBA Program, which, to accommodate working students, holds classes every other Friday and Saturday. “It was great, because I was meeting successful executives,” Riccobono says. “I was twenty-six, maybe the youngest guy there — everyone else was thirty to forty-five — and I was learning a ton. It’s ’05, ’06, and every guy trading some kind of complex product was making money you wouldn’t believe. So I said, ‘This is great. This is what I’ll do.’ I focused on finance, took all these complex-products classes, and was in way over my head. In ’07, I interviewed for hedge funds. I thought, ‘I don’t know if this is my lifestyle — wear a suit every day to work, get in at five, leave at nine, and not be able to do anything creative on the side.’ But then the decision was made for me: the market crashed, people were losing their jobs, and I said, ‘This is the perfect time to start my video wine blog.’”

With the financial world in tatters, Riccobono, having inherited a love of wine from his father, took six months to learn everything he could about the wrath of grapes, approaching his subject with the single-minded ferocity of an athlete, pressing every drop of knowledge from his books and decanting many a pretty-labeled bottle. In 2009, he posted the first installment of Pardon That Vine, an earthy, proudly unpretentious video diary that numbers nearly four hundred episodes. The setup is simple: Riccobono appears in front of a video camera, seated at home in Hoboken or in one of the many wine regions he has visited — Napa, Sonoma, Piedmont, Campania, Bordeaux, Tuscany — dressed in a T-shirt and jeans (“In the wine world, there’s a lot of snobbery, but people see a guy in a T-shirt and a backward cap and they’re not intimidated”) or a yellow or pink polo or, increasingly, an UNTUCKit button-down, wine swirling in the glass bowl of the goblet in his hand as he introduces the wine and shares with viewers the real-time sensations of his nose and papillae (“I’m getting a huge blast of fruit here.” “I’m getting a little cinnamon component.” “I’m still getting this peanutty thing on the end.” “It’s got complexity, it’s got mouth feel, it’s got finish, it’s got acidity, and it’s got this pine-needle-meets-fire-smoke-pizza-oven scenario”), all delivered in a red-blooded way that makes you feel that you, too, can reach the high-hanging fruit of culture. The blog attracted thousands of followers, and soon winemakers from all over the world began shipping bottles to Riccobono for his review. 

The experience taught the entrepreneur about social networking and marketing and prepared him for his next venture. “Here I was, in the worst economic environment in decades, trying to launch a fashion company, and I’m not even in fashion,” he says. “Social networking allows you to start any business you want at a reasonable cost.” With UNTUCKit, he had a snappy brand name that his PR firm could run with, and, unlike other concepts he’d concocted, nobody called this one kooky. Riccobono put together a business plan, raised money, built a website, consulted shirt specialists and pattern makers, spent ten months designing and redesigning, sought out the highest-quality fabrics from Turkey, Egypt, Italy, and Japan, and found a manufacturer in Poland.

When UNTUCKit went online in June, the response was swift. The Wall Street Journal gave Riccobono’s shirts a plug. So did GQ, USA Today, and NBC’s Today. And Today’s Man, seeing a new day and a new way, swiveled around excitedly in his cubicle, grabbed his mouse, and clicked. He ordered a shirt, six shirts. Then, lo and behold, Matt Damon requested a shirt. So did Kevin Connolly of Entourage, and Pauly D from Jersey Shore. If that wasn’t enough, TV hosts Billy Bush of Access Hollywood and Mario Lopez of Entertainment Tonight Extra began wearing UNTUCKit shirts on their shows. 

It’s been a good start for a clothing company that’s less than seven months old, but Riccobono measures success not by the yard but by the mile. He envisions a whole UNTUCKit line, a major brand, a smash hit, and many happy returns. 

“I haven’t made it, by any means,” he says. “In fifteen years, I could be rich, or I could be back to square one. It’s scary. I don’t sleep at night. But that’s what I love — the risk.”

Yet for all his stubble and independence, for all the satisfaction of starting his own business, Riccobono must have some regrets about missing the Wall Street gravy train. 

Doesn’t he? 

The entrepreneur smiles, and Today’s Man, somewhere on his lunch break, tie barely loosened, smiles with him, perhaps a little wistfully, already knowing the answer. 

“The truth is,” Riccobono says, “I wouldn’t have lasted long.”   

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