Jesse Silvertown has always been passionate about hats. But he didn’t realize just how much goes into making a nice cap — a really nice cap — until he finally quit his day job and leaped. Or launched. His company, Ledge Headwear, released its first line in January, putting him a market that he compares to the sneaker craze of 15 years ago.

“Headwear is really emerging,” Jesse said. “And Kendall Roy in ‘Succession’ accelerated it.” It turns out there are not dedicated luxury headwear brands, and that’s where he hopes to fill a niche. “There are a lot of good baseball caps, no doubt, but it’s usually an accessory for a brand that focuses on something else.”

Jesse — who married into Tribeca; his wife, Jenna Silvertown (above), grew up here and runs her family’s farm in New Paltz — worked at Ernst & Young in forensic accounting for 13 years and loved it there, but this was a good time in his life to pursue a passion. He left the CFO gig in 2022, started R&D for the caps, visiting factories, researching fabrics, training himself in design, and finally settling on a family business in Piedmont, Italy, to do the manufacturing. The fabric is a tight weave 100 percent cotton from a “really nice mill” that he refused to disclose — trade secret.

“It is very understated luxury,” he said. “And it feels great. I never take it off.”

He’s engaged friends as models, found a student from FIT to photograph the product by emailing career services there, and is generally digging in to the details the hard way. “We are big on ambition and short on experience but I think we are capable,” he said. “It felt appropriate to find a student who was coming from the same place.”

The business will stay direct-to-consumer for now, and now offers designs that focus on the 5Fs — fit, form, fashion, fabric, function — plus the hat has to sit nicely on a table and keep its shape over time. And yes, it costs. Caps are $187 plus shipping, which he said will come with a “positive margin without gouging people.” He’s not expecting this to be the end-all of his career path, but he couldn’t *not* try it.

“This is a death-bed test for me,” Jesse said. “I’m not going to do only this for the rest of my life. This is my passion and I just wanted to see what I could build.”

Plus, the prototype now fits him perfectly.