In 1990 Connecticut native David Levy was dreaming of working on Wall Street and making a name for himself in the finance world. He was busy earning his M.A in economics degree at Kent University in England.
“It was an exciting and eye-opening time, both academically and culturally,” Levy recalls. “My plan was to break into investment banking and build a long-term career in finance. I was driven, ambitious, and excited to become a part of that high-energy world. I was dreaming of living the full-on, stereotypical ‘Wall Street’ life—suits, skyscrapers, and the fast-paced hustle. I wanted to be in the middle of the action.”
First, though, Levy embraced Europe with open arms. “I made lifelong friends and traveled throughout the continent,” he says. “The Berlin Wall had just come down; the energy across Europe was incredible. There was this overwhelming feeling of change and possibility. It was a once-in-a-lifetime experience to witness that kind of history unfolding in real time.”
That same year, Hawley Lane Shoes, Levy’s then second-generation, family-owned business, was a different operation than it is today. First off, it was just one location, not the five it is now, and it was focused heavily on fashion. “We catered to style-conscious shoppers, whereas today we’re entirely focused on service, comfort, and solving foot pain,” Levy says. “Shopping with us has become a full experience. We’re committed to helping people find real solutions, in addition to great shoes.” Levy credits the shift in format to his mother, Sandra Levy, and uncle Bob Smolensky. “They were the true visionaries who transformed Hawley Lane Shoes into a comfort-focused, life-changing experience for our customers.”
It wasn’t until 2020 that Levy joined the business full-time. In fact, his footwear career started by chance. Back in the U.S. and job hunting amid a recession in 1991, a friend mentioned that her sister had a job opening at Stride Rite in product development. “Something told me to meet her,” Levy says. “I got the job and just six months later, I was on a plane to South Korea—completely on my own and no idea what I was doing.” It was intimidating and exciting all at once, and it led to a rewarding career in product and marketing, working at Keds and Converse. Levy then became Director of Product for the launch of Tommy Hilfiger footwear—a project he was “incredibly grateful” to have been a part of.
Levy’s decision to leave the corporate world started with a request. “My mother and uncle offered me the opportunity to join the family business that they’d built and evolved with so much heart and intention,” he says. “I’m incredibly grateful for the trust they placed in me and the chance to be part of something so meaningful.”
Levy considers himself lucky. Specifically, working in a profession that blends creativity, purpose, and real-world impact. “Helping people feel better, whether it’s through great product or personalized service, has been deeply rewarding,” he says, adding that traveling the world and working with iconic brands and learning from brilliant colleagues were bonuses. “The greatest gift has been bringing all of that back to our family business and building something meaningful for our communities. The shoe business has given me a life of purpose, connection, and fulfillment. For that, I’m truly thankful.” •
