Q&A with UNTUCKit Co-Founder Chris Riccobono

Discover Riccobono's inspiration behind the clothing company's name and his tips on getting ahead in business.

Photo by Evan Browning

Chris Riccobono came up with the idea behind UNTUCKit, the apparel company he co-founded with Aaron Sanandres, while looking to escape corporate America and the suit-and-tie milieu associated with it. He spent enough time there, from working as a trainee in the technical sales and leadership program at General Electric in the early 2000s to learning about finance and interviewing for hedge funds as a student in Columbia’s Executive MBA program in 2006.

In 2009, Riccobono arrived at the notion of a casual dress shirt cropped just below the beltline, which eliminated the need for a shirt to be tucked in to look tidy. The design isn’t meant to be ultra trendy—it’s more about having a better fit—and is geared toward both the fashion-conscious and regular guys who don’t wish to spend too much time browsing the shirt racks.

UNTUCKit has grown quickly from an online business launched in 2011 to a modest group of brick-and-mortar stores in cities including New York City (where the company is based), Los Angeles, Dallas, Austin, San Francisco and Chicago. This year, things are ramping up impressively as Riccobono, Sanandres and their rapidly growing team prepare to announce a number of new store locations in the U.S., along with new apparel such as jackets, polos, sweatshirts and T-shirts, all cropped to fit in with the company’s design look. A new line dedicated to women has also been unveiled, including vests, scarves and tank tops.

When did you first come up with the idea behind UNTUCKit?

I came up with the idea in 2009, but I wasn’t in the fashion industry and had no idea how to raise the money needed to launch the company. Coming up with the name got me to move forward.

How did you land on the name?

If we had called the company Chris Riccobono Shirts, even if it was the same style, we would have been ignored. [UNTUCKit] was a name that could be marketed, and when I talked to investors I pointed out that there wasn’t a retail company where the name is the function.


“There’s a lifestyle feel behind what we’re doing.”


Was UNTUCKit your first attempt at entrepreneurship?

I tried to escape the corporate world a few times. I launched a video wine blog in 2009 [called Pardon That Vine] because of my love of wine, especially from Italy, France and California, and because I wanted to try my own business—I don’t like working for other people. I tried to make it into a business, but it wasn’t meant to be; it did give me the confidence to attempt something else, though.

What’s next for the brand?

Shirts will always be a focus, but at this point 25 per cent of what we’re selling are other products. There’s a lifestyle feel behind what we’re doing, and we launched in a time when top companies and even French restaurants are allowing a dress code of jeans and untucked shirts. We’re very much just getting started. It’s not the end of the curve as far as what the business can do.

Are there any plans to take UNTUCKit outside of the U.S.?

We’re going to eventually move into Canada, where something like five percent of our online sales have been, and that’s with no effort on our part. When we launched, we partnered with a Canadian, Brad Richards, a retired MVP hockey player who was with the Tampa Bay Lightning. He’s been the face of our brand, and it’s worked really well.

What advice would you give to an emerging entrepreneur?

Be prepared for the bad days and obstacles you will come across, and don’t let it get you down. The reality is taking two steps forward and one step back, and there is a different challenge to overcome every day.

UNTUCKit Must-Haves

This casual yet fashionable range of apparel makes for great travel wear.

For him: The Altos

The Henley pullover comes in charcoal or heather grey. A cotton and polyester blend, the Altos is soft and comfortable, and packs small.

For her: Camille Breton

This cashmere sweater is chic but casual and fits in nicely whether you’re visiting a museum gallery or wandering a summer garden.

For him: The Dolcetto

Bringing along this wrinkle-free garment allows you to change quickly after a long fight without worrying about locating an iron.    

For her: Veuve Clicquot

There are tons of pockets in this quilted nylon vest to keep your passport, wallet and travel guides close at hand.

Editor’s note: This story was originally published in the August 2017 issue of WestJet Magazine and has since been updated. 

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