UNTUCKit: Chris Riccobono
How do you turn a side hustle into a retail empire that popularized the untucked shirt? Chris Riccobono, co-founder of UNTUCKit, started the company while working at GE Healthcare, launching with a $150,000 investment and a lot of skepticism. From near-bankruptcy after a $750M acquisition fell through in 2020, UNTUCKit rebounded to more than 80 stores and a growing wholesale business. In this episode, Riccobono explains why an idea everyone laughed at became a category-defining brand — and what it took to survive when success almost slipped away.
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Episode Recap
Chris Riccobono never wanted to climb the corporate ladder. Growing up in New Jersey and playing tennis at Providence College, he knew early that selling medical equipment at GE Healthcare was a means, not an end. While his colleagues plotted promotions, Riccobono was already plotting an exit — and a string of side projects, including a wine vlog called "Pardon That Vine" that drew just a handful of viewers.
The Shirt That Launched a Category
The idea for UNTUCKit came to Riccobono on a bachelor party in Las Vegas, where he noticed every guy in the group complained that dress shirts were too long to wear untucked. He brought on Columbia Business School classmate Aaron Sanandres as co-founder, and in 2010 they produced their first prototype — a shirt that looked polished yet casual enough to leave untucked. The first run was a disaster; customers returned shirts saying they were using them as car rags. Rather than quit, Riccobono kept a list of dissatisfied buyers and promised to make it right.
Building the Brand From a Hoboken Apartment
For six years, Riccobono balanced GE sales calls with UNTUCKit fulfillment, ironing and packaging shirts by hand in a storage unit after work. They launched online with no advertising budget, pricing each shirt around $80 and refusing to take outside money. Customers who received great service spread the word, and the brand slowly built a cult following. By the time he left GE in 2015, UNTUCKit was generating more than $20 million annually with just two employees and no fundraising.
From SoHo Store to Near-Billion-Dollar Exit
UNTUCKit opened its first brick-and-mortar location in SoHo in September 2015, and the response was immediate. Within two and a half years, the company opened roughly 90 stores across North America and the United Kingdom. Kleiner Perkins invested $8 million in 2016, followed by a $30 million round in 2017. The brand became so influential that competitors from Vineyard Vines to J.Crew launched their own "untucked" lines — and UNTUCKit forced some to pull ads that copied its tagline. By late 2019, Riccobono and Sanandres received about 15 letters of intent to acquire the company for roughly $750 million.
The COVID Collapse and the Fight to Survive
In March 2020, every potential acquirer pulled out as the world shut down. Revenue dropped 40 to 50 percent almost overnight, and with 90 stores, hundreds of employees, and millions in factory debt, the company ran out of cash. A bankruptcy attorney told Riccobono he would own nothing if they filed. Instead, he and Sanandres called every landlord and factory individually, negotiating deferrals while Kleiner Perkins provided emergency capital at a steep discount. By 2022, UNTUCKit was profitable again; 2023 became its most profitable year ever.
What Comes Next
Today, UNTUCKit is pursuing wholesale partnerships with Nordstrom, Macy's, and Stitch Fix, and plans to open in Mexico City. Riccobono still believes the brand can reach a billion dollars in revenue, and while he wants to sell eventually, he says he will stay involved for the long haul. As for those early terrible shirts? He kept a list of customers who hated them — and eventually won many of them back.
Key Takeaways
- 1Side Hustle Origins: Chris Riccobono founded UNTUCKit in 2010 while working at GE Healthcare, launching with roughly $150,000 and no outside investment.
- 2First Batch Disaster: The brand's initial shirts were so poorly made that customers returned them to use as car rags, but Riccobono kept a list of dissatisfied buyers and improved the product.
- 3Bootstrap to 80 Stores: UNTUCKit grew without fundraising until Kleiner Perkins invested $8 million in 2016 and $30 million total by 2017.
- 4COVID Near-Bankruptcy: A roughly $750 million acquisition deal fell apart in March 2020, revenue dropped 40 to 50 percent overnight, and the company ran out of cash.
- 5Recovery and Wholesale: Riccobono survived by negotiating directly with landlords and factories, and by 2023 UNTUCKit had its most profitable year ever while expanding into Nordstrom, Macy's, and Stitch Fix.
