“I was never a great dresser”

Untuckit founder Chris Riccobono on his abnormal path to fashion success.

“I was never a great dresser”

It’s actually a running joke in my family, but never in a million years did I think I would end up being a fashion designer. Growing up, I was definitely not a fashionista or even a great dresser. When I was in college, Abercrombie & Fitch was popular, so I’d wear that. My only fashion commentary back then was wishing my shirts were shorter. No one took it seriously because I had a new idea every day. Friends would make fun of me for that, but I really believed that I just needed that one-in-a-billion idea.

When I turned 30, I started to get nervous that I was nine years into my career without finding that idea. Luckily, it clicked a few months later while on a Vegas trip with friends. I brought five shirts to wear, but ended up wearing the same pink shirt three nights in a row—yet another reason for my friends to tease me, but I swear it didn’t stink! That pink shirt was an anomaly: I’m a medium or a large, but this was a small, and looked good when worn untucked. The fit must’ve been a factory error, but I kept noticing how sloppy my other dress shirts looked in comparison. I asked around and lots of guys had this sloppy untucked shirt problem, too. I had my idea.

At the time, I had about 5,000 followers on social media from Pardon That Vine, a wine blog I started after leaving Wall Street when the market collapsed in 2008. I leveraged some of those followers into my untucked shirt venture by naming my shirts after wines and linking my blog at the bottom of Untuckit’s website—something I learned later that you just don’t do with a fashion label.

I was definitely not going about things the “normal” way, and people weren’t supportive at first. Some called me crazy. Others dismissed the concept altogether. Fashion experts would tell me that I couldn’t name it Untuckit—that you don’t name something for its function, that it didn’t sound right. They suggested a nicer, more sophisticated logo with my name in script like Brooks Brothers. But I couldn’t—the name was the whole point.

Once I settled on Untuckit, I tried on hundreds of shirts in department stores across New York. Nothing fit right. I went to the Garment District carrying that pink shirt from Vegas trying to get a sample made. Only in hindsight can I appreciate how ridiculous that was. I met with dozens of people and no one factored in the length of the shirt. They used the same specifications that everyone had been using for years.

Designers usually start by creating something beautiful, but at Untuckit we say, “Let’s get something functional that fits perfectly, then we’ll take the design from there.” Another fashion no-no.

Now I find it funny when people tell me that they love the name. It had never been done before in fashion. But that’s how we’ve made things work. I’ve got to say: So far, abnormal is working for us.

Untuckit is one of America’s fastest-growing apparel brands, despite the name.