Image: Angelica Alzona/GMG
“Men just want to find a fit and then not change from that,” Chris Riccobono, founder of the menswear brand Untuckit (or, as the brand styles it, UNTUCKit), says. “They don’t really want to have to overthink their outfit.”
Riccobono has also found that men don’t like to iron their clothes. That men now typically own, say, 10 casual shirts and one dress shirt, though they’d rather wear the casual ones to everything from ball games to nice dinners. Most importantly, they need shorter shirts; or, at least, they haven’t yet realized they need shorter shirts. The entire Untuckit brand is built on the apparently groundbreaking idea that a typical men’s button-up should be shorter.
Regular men’s shirts, in Riccobono’s eyes, are too long. They’re designed to be tucked in and thus arguably designed for a man of an increasingly bygone era, when men were expected to tuck in their shirts to meet a Don Draperian standard of formality. This shirt-length problem first became a nagging concern to Riccobono when he went on a trip to Las Vegas with his buddies. He had three shirts with him, one of which was a size small but it fell to “the perfect length.” “Every time the next night came, I would go put on a new shirt but it looked so long,” he says. “So I put the shirt back on for three nights in a row.”
“I asked all my friends who were there, do you have the same problem?” Riccobono says, a Jersey accent underlining every word, casual in a grey henley and baseball cap. We are sitting in Untuckit’s modest SoHo office, where the white, glass-walled conference rooms bear the names of different wineries (Larkmead, Spottswoods) to reflect Riccobono’s noted affinity for wine. “Instead of being like you’re crazy, they all had the exact same problem,” he says.
It was also a problem Riccobono, who was working in medical sales at GE Healthcare at the time and attending Columbia business school, felt he could solve and monetize. Riccobono and his co-founder Aaron Sanandres did a survey of 500 men in Hoboken, New Jersey, where Riccobono was living at the time, and found that other men had this elusive problem as well (Untuckit declined to provide this survey data, explaining they don’t share it formally).
“My thought as an entrepreneur was if I legitimately had a problem then I can’t be the only guy with the problem,” he says. “And this was legitimately a problem. I did not have a shirt other than this one shirt that I could wear that was not too long.”

That problem is now a multi-million dollar company, with 50 stores across the country. In 2018 the company, founded in 2011, reportedly had $150 million in sales and was seeking a valuation of $600 million, which Riccobono says will help them go overseas. A representative for Untuckit declined to provide revenue numbers but shared that the company has a four-year compounded annual growth rate of 150 percent. The menswear industry has noticed: recently J. Crew and The Gap have started selling shirts designed to wear “untucked.”
Untuckit’s success and creeping ubiquity are still surprising. Starting a company with the crusade that men need shorter shirts (and are apparently incapable of finding them) seemed like a joke. “It was impossible early on when I went to friends and family,” Riccobono says about first seeking investors. “They’d say, you’re making a shorter shirt?” Even the brand’s name, which bears the simplicity of the brand’s mission, trips off the tongue like a work in progress. Though they’ve expanded into other clothing items, the famous shirt at the center of Untuckit’s rise still begs the question: Does this really need to exist?
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