As it says in our stores, we started UNTUCKit because we couldn’t find shirts that looked good untucked. It’s a tough style to get right. That’s why we created the perfect untucked shirt. That was 10 years ago. In that time, we’ve helped millions of guys untuck. But it didn’t happen overnight.
Here’s the story of how two entrepreneurs with no fashion experience upended the industry by introducing a shirt everyone thought was so simple to make. But they didn’t know the whole story. Here’s how Shirts Designed to be Worn Untucked really started.
2010 | THE BIG PROBLEM
A little more than 10 years ago, UNTUCKit Founder Chris Riccobono, who’d had countless business ideas before UNTUCKit, identified the problem no brand had yet solved: no one makes shirts designed to be worn untucked.
He started discovering his friends had the same problem—all of their nice dress and causal shirts were different lengths.
“I visited every major store and actually brought a tape measure with me,” says Chris. “The length of men’s shirts was all over the place, but none of them were quite right.”
So Chris brought his idea to make untucked shirts to his friend and Columbia Business School classmate, Aaron Sanandres, who was working at Price Waterhouse Cooper at the time. They’d vetted plenty of new business ideas in the past, but none of them stuck. However this one piqued his interest.
“It’s not often you find a true hole in the market and actually get ahead of the innovation,” says Aaron. “But I knew we had something from that initial phone call. I told him I was in.”
So Chris went up and down 7th Avenue in Manhattan, sample shirts in hand, trying to find a tailor who could create his vision. He eventually found one and after a year of development, he had seven storage units near his Hoboken, N.J., apartment chock full of the first run of shirts.
2011 | GOING ONLINE
With a business plan in hand, Chris and Aaron convinced a handful of family and friends to invest $150k into their fledgling idea with a funny name: UNTUCKit.
“The brand’s name is the smartest thing we’ve ever done,” says Chris. “It’s divisive, but more importantly disruptive and it got people talking.”
So Chris and Aaron would work their jobs during the day—then at night they’d pour their free hours into Project UNTUCKit. Eventually, UNTUCKit.com launched with 10 cotton shirts, selling a grand total of 150 units in the site’s first month—mostly to friends and family.
“Those first few months were a labor of love,” says Aaron. “It was incredibly rewarding to know we were taking a risk and launching something new.”
2012 | THE EARLY DAYS
For the first few years, shipping was fulfilled out of Chris’ third bedroom. He received, ironed, and processed all returns by hand. Along with Aaron, they answered all emails and phone calls—all of the early brand’s customer service needs.
“I can remember those days being so stressful,” says Chris. “That’s why I always tell new business owners to stop and enjoy the moment—even in the stressful times.”
2013 | PUSHING FORWARD
After a few years of 18-hour days to keep the UNTUCKit dream alive, the UNTUCKit fulfillment operation found a new home in an official warehouse. And it was a good thing, because the operation had grown tremendously early on.
Meanwhile, UNTUCKit started marketing—mostly with radio spots and airline magazine ads. And the company picked up its first brand ambassador: two-time Stanley Cup champion Brad Richards of the New York Rangers.
The new marketing tactics and ambassador all paid off big time. By the end of 2013, the brand officially sold out of untucked shirts.
2014 | FULL TIME WORK
By now, the shirts had been redesigned to improve the design, and sales increase sixfold. UNTUCKit eventually passed a big landmark—selling its 1 millionth shirt. It was around that time that Chris decided to leave his job at GE and focus on UNTUCKit full time.
“At this point, I’d be living and breathing UNTUCKit for a while,” says Chris. “We’d heard such amazing customer response, so I was confident, but it was a risk for sure.”
The company had a few dozen employees, all working out of a WeWork in Soho—but with big plans for an actual UNTUCKit store on the horizon.
2015 | BRICK AND MORTAR
What had started as a meager ecomm-based business was about to dip into the world of retail. The first UNTUCKit store opened on Prince Street in New York City’s SoHo neighborhood.
“It’s definitely one of my most proud moments,” says Chris. “We had great foot traffic and that location really put us on the map.”
The SoHo store started to grab some attention right away. Leonardo DiCaprio, fresh off the Oscar-winning release of The Revenant, loved the shirts so much that he’d been spotted at the store three times—in one week.
This year also saw new product releases outside of button-downs, like tees, polos, and sweatshirts.
2016 | UPWARD TRAJECTORY
Once the business built up enough steam, Aaron decided to leave his job as partner at PwC after 18 years at the company to join UNTUCKit full time to take the business to the next level.
“This was the ultimate leap of faith for me,” says Aaron. “But by this time, I knew this business would take off. I was just excited to dedicate myself to it fully.”
Then, an iconic moment: Founder Chris Riccobono shared his big problem in our Chris Walking commercial that told the brand story. It’s been widely shared on social media, with nearly 400,000 views on YouTube to date.
“The commercial—just like the name—started a conversation.” says Chris. “Everyone was talking about it. And everyone had a different take.”
The brand launched new products in jackets, sweatshirts, and even a Tall fit. Also, new brick-and-mortar stores opened in Austin, Chicago, LA, and San Francisco.
2017 | A WHOLE NEW HQ
UNTUCKit HQ officially opened in SoHo, down the street from the store. At this point, the corporate office had nearly 100 employees. The team embarked on its first international photoshoot in Cartagena, Colombia.
At the Super Bowl, Chris met Drew Brees and told him about UNTUCKit. Later on, Drew did some research and returned to Chris with pages of questions about the business. Drew was impressed enough to sign on as an investor—and brand ambassador.
“To have such an icon representing the brand was a huge milestone,” says Chris. “And he was so engaged in the business side of things. It’s been a great partnership.”
In 2017, the iconic Wrinkle-Free™ and Performance™ lines launched—the brand’s biggest franchises so far. With a special treatment, they came out of the dryer ready to wear, making our untucked shirts even easier to wear and care for. The brand also expanded into shorts and a women’s line, featuring shirtdresses and shirts.
2018 | THE IDEA SPREADS
UNTUCKit began its collaboration with MLB in this year by launching MLB Signature Series shirts—Wrinkle-Free™ shirts featuring top team logos.
“Sports has always been an important part of UNTUCKit,” says Chris. “Athletes get the concept more than anyone and I think that’s why we’ve attracted so many.”
Hockey icon Wayne Gretzky became another athlete investor and ambassador around this time, which was also when our first Canadian store launched in Toronto.
"I'm excited to be working with UNTUCKit—especially as they open so close to home,” Gretzky said at the time. “Their incredible product drew me to the brand, and, after learning about their rapid growth, I knew I wanted to be involved.”
Around this time, the brand also solidified its spot in pop culture, appearing as an answer on Jeopardy: “This clothing company’s shirttails fall between the belt and the bottom of the zipper, so no need to stuff them in.”
2019 | ACROSS THE POND
In keeping close ties to the sports world, UNTUCKit’s billboard appeared in Yankee Stadium’s right field. The brand signed Manchester City’s Kevin DeBruyne as a brand ambassador. He’s one of the biggest soccer stars in the world, and joined UNTUCKit as it opened two stores in London, expanding its international footprint.
Back home, the brand’s “The Right Call” ad (featuring Drew Brees) aired, showing the difference wearing the perfect-fitting shirt can actually make.
Men’s Health also declared that UNTUCKit makes “the sharpest flannel shirt you’ll ever own.”
It’s around this time that many major men’s brands change their strategy to lead with untucked shirts. Chris and Aaron weren’t shocked by the copycats, but saw this as proof that untucked shirts had grown beyond a fad—they were in our closets for good.
2020 | ...QUARANTINE
The COVID-19 pandemic turned the world on its head, and everyone is forced inside. People who could work from home do so, and everyone traded their untucked button-downs for tees and Henleys. To respond to the times, UNTUCKit adjusted its collection to make it even more comfortable and gave away 45,000 shirts to first responders.
“It was by far the hardest year for the business,” says Chris. “But we safely opened up every one of our stores as soon as we could and we’re already seeing customers returning for shirts to help them get back out there.”
UNTUCKit also deployed new technology to further the business by adopting contactless delivery, creating a live chat tool, and launching an automatic Fit Finder.
2021 | 10 YEARS IN THE MAKING
This year, UNTUCKit is proud to sell its 7 millionth shirt. And to become the official shirt of guys looking sharp and feeling comfortable post-quarantine.
“It’s been an incredible journey and we’re so grateful to our customers,” says Aaron. “As the untucked shirt becomes a part of everyday life, we look forward to helping millions more guys look great and feel comfortable with the perfect-fitting shirt.”
More than 80 stores worldwide—and more on the way. Plus 7 million shirts sold—and there’s no stopping. It’s been an incredible 10 years. Here’s to the next 10.
