How a former Bay Street accountant ended up dressing Canadian hockey players

Toronto-born and a graduate of the Ivey School of Business, Jesse Silvertown began his career as a forensic accountant at Ernst and Young—first in Toronto, then in New York—before pivoting to fashion in 2022. Two years later, in 2024, he launched New York–based luxury ball cap brand Ledge Headwear, carving out a niche with a high-end cap-only concept.

“I’ve always been interested in fashion,” says Silvertown. “When I was working in Toronto’s finance district, I noticed how style was evolving in corporate culture—sneakers were starting to show up in the office. I was drawn to the idea of taking a single product and elevating it into a true luxury brand. I’ve always been a baseball cap guy, so I decided to focus on making a great one.”

Related: How an unlikely series of events made the “Born ready” baby Vladdy T-shirt to go viral

Silvertown comes by his love of single-product brands honestly. His father, Paul Silvertown, worked for years in sales at Canada Goose, and Jesse was inspired by the company’s singular focus. “It was a product that spoke for itself—one that didn’t require marketing gimmicks or massive campaigns. That’s the ethos of Ledge.”

With that philosophy in mind, Silvertown spent 18 months in research and development before officially launching the brand. “I knew I needed the right fabric so the cap would keep its shape,” he says. “It needed to be comfortable, it needed to last, and it needed to be produced in a factory with generations of knowledge and craftsmanship.”

After cycling through multiple factories, he ultimately landed in Milan, which became the home base for production. Not long afterward, his caps began finding their way into the hands of Canadian hockey players. “We did a collaboration last year with House of Chan that sold out within weeks of launch,” says Silvertown. “When we did a recent reissue, I thought it would be fun to send one to a Toronto-born player on the Leafs. I’ve seen a Leaf or two at House of Chan over the years, so I know they dine there.”

To get the cap into the right hands, Silvertown reached out to Jennifer Kardosh, head of hockey operations and marketing at Creative Arts Agency. What started as a single send-out quickly grew. Kardosh asked whether Silvertown could provide 41 Ledge caps for the agency to include in gift bags for the hockey players it represents. Silvertown sent a variety of colours and made sure the special-edition T Dot cap—an homage to his hometown—went to the three Toronto-born Olympians: Natalie Spooner, Brianne Jenner and Claire Thompson.

For now, Silvertown’s caps are for sale exclusively online, but the long-time Uncle Otis fan hopes to get Ledge headwear into independent shops in Toronto soon. Hats off to him.