Though Chris Riccobono didn't have any fashion experience when he launched menswear brand Untuckit, he managed to solve a problem in the business casual space. The company's dress shirts designed to be worn untucked have been copied by a plethora of competitors and fueled its profitable business.

Since entering the market 2011, the NYC-based DTC brand has seen its fair share of highs and lows: Prior to the start of the pandemic, Untuckit had expanded to 90 retail locations around the world, including six in Canada and a new store in England. But subsequent lockdowns forced Riccobono to temporarily close all locations.

"There wasn't one time during the pandemic that we gave in and said, 'I wish we didn't open these stores.' We stood behind them," Riccobono said on the latest episode of the Glossy Podcast. "You can't operate a massive growing men's retail business without having stores."

The slight setback didn't stop Untuckit's growth. Once the quarantine and guidelines lifted, and consumers began feeling comfortable in public spaces again, Untuckit sales ramped up. In 2021, Untuckit opened three new locations, including in Long Beach, California, Sarasota, Florida and Manchester, U.K.

Now, Riccobono is expanding his portfolio. In June, along with Derek Jeter, Misty Copeland and Wayne Gretzky, he introduced an all-new brand, Greatness Wins. It's centered on performance athletic apparel.