UNTUCKit
UNTUCKit is an American casual men's apparel brand known for shirts designed to be worn untucked. Founded in 2011 by Chris Riccobono, the company grew from a side hustle into an 80-plus-store retail phenomenon with locations across North America and the United Kingdom.
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
Products & Services
Hillside Select Wrinkle-Free Shirt
A solid light blue button-down made from 100% wrinkle-free cotton. Features the signature untucked length, Stay-Put Collar, and chest pocket. The quintessential UNTUCKit everyday shirt.
EcoSoft Short-Sleeve Henley
Our softest henley ever, made from a stretch cotton and TENCEL™ Lyocell blend. Breathable, comfortable, and designed with the perfect untucked length for casual layering.
Durif Wrinkle-Free Button Down
A timeless navy-and-white check button-down crafted from 100% breathable cotton with wrinkle-free technology. Ideal for layering under a sport coat or wearing on its own.
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
Today’s callers: Adrian from California wants to grow his apparel company to complete with big-name athletic brands. Then, Preet from the Rockies looks for strategies to reach seniors and their children with his daily check-in app. And Derek from Virginia considers social media and professional partnerships to advertise his hockey equipment brand. Plus, Chris talks about launching a new athletic apparel brand while continuing to grow UNTUCKit. Thank you to the founders of Eras Shorts, Snug Safety, and Hockey Ninja for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to UNTUCKit’s founding story as told by Steve on the show in 2017. Annlie Huang. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack.
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.
