UNTUCKit
UNTUCKit is a fashion brand. It makes untucked dress shirts. Every piece is cut to fall right at the hip, no tucking required. No stiff, scratchy fabric. Just simple, polished style for everyday wear.
The Story
UNTUCKit began as a side-hustle idea by Chris Riccobono while he was working at GE Healthcare and studying at Columbia Business School. The premise was simple but unconventional: create a shirt that looked sharp yet casual enough to wear untucked. In 2010, Riccobono developed the original untucked shirt prototype, and by February 2011 he brought on Columbia classmate Aaron Sanandres as co-founder. They launched with roughly $150,000, no office, and Riccobono kept his GE day job for six years while building the company from his Hoboken apartment.
The early product was rough, but the slow-burn strategy protected the brand. By the time he resigned from GE in 2016, the company was generating more than $20 million with only two founders and no fundraising. UNTUCKit opened its first store in SoHo in September 2015 and expanded to more than 80 locations across North America and the United Kingdom. The brand also introduced a women's line in 2017.
In 2020, a roughly $750 million acquisition deal fell apart, pushing the company to the brink. Riccobono and his team survived by negotiating lease deferrals and tightening operations, and by mid-2021 the brand had surpassed its pre-pandemic performance. Today, UNTUCKit is known for wrinkle-free button-downs, polos, tees, henleys, and flannels, all designed with the signature untucked length.
Key Facts & Metrics
Company Timeline
2010 — Original Untucked Shirt Prototype Developed
Chris Riccobono created the first untucked shirt prototype while working at GE Healthcare and studying at Columbia Business School.
2011 — UNTUCKit Founded
Riccobono brought on Columbia classmate Aaron Sanandres as co-founder and launched UNTUCKit with roughly $150,000 in seed capital.
2015 — First Brick-and-Mortar Store Opened
UNTUCKit opened its first retail location in SoHo, Manhattan, marking a shift from direct-to-consumer e-commerce to physical retail.
2017 — Women's Line Launched
The brand expanded its product offering to include women's button-down shirts, opening a major new customer segment.
2020 — Near-Acquisition Collapse and Recovery
A roughly $750 million acquisition deal fell apart, pushing the company to the brink. The team survived by negotiating lease deferrals and tightening operations.
Episodes Featuring UNTUCKit
Advice Line with Chris Riccobono of UNTUCKit
Chris Riccobono returns to the Advice Line with an unvarnished update on UNTUCKit: tariffs, wholesale expansion, and the operational grind of keeping a growing apparel brand moving. Three callers then push him on harder problems. Adrian Alvarez wants Aero Shorts to outgrow its volleyball niche and compete with bigger athletic brands. Preet Anand is searching for awareness channels for Snug Safety that fit a trust-based, older demographic. Derek needs a real plan for Hockey Ninja now that NHL clearance is in hand, and he is choosing between social media, equipment managers, and a player partnership.
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.
