LEDGE HEADWEAR: HATS ON!
Jesse Silvertown is one of the most focused and determined young entrepreneurs I’ve interviewed. After a 13-year career in forensic accounting and inspired by the success of the TV series Succession, he decided to jump into the hat business. But not just any old hats of course: his singular focus is handcrafted luxury baseball caps, made in Piemonte Italy of the finest quality fabrics (including a limited-edition baby alpaca cloth by Dormeuil). “Most cap business is more about the message than the product. We’re about unadorned, understated luxury, caps with no writing or logo on the front or brim. We’re the only premier hat company focused solely on luxury caps; that’s all we do.”
Jesse started out researching this venture in 2022, visiting family-owned factories and fabric mills in Italy, studying design, teaching himself the business with a little advice from his dad, a former exec at Canada Goose. It took him 15 months and 32 different sample iterations to get it right. “I realize I was big on ambition and short on experience,” Jesse admits. But using friends as models and FIT students as photographers, he managed to get both press and orders, even exporting caps to Japan and England, while spending virtually nothing on marketing.
While he started out selling direct-to-consumer (with each cap shipped in a beautifully lined box), Jesse is now focused on building wholesale business with independent luxury stores. But with the uncertainty of impending tariffs and a severe stock market slide, how easy will it be for menswear merchants to sell $187 baseball caps? “Consider that similar caps from ‘famous luxury designers’ are retailing at $600 and $700,” points out Jesse, “ours is a bargain. Customers will see the difference immediately: the way the cap looks and feels, the way it fits the head and holds its shape. I believe it’s a growing market: caps are today where sneakers were 20 years ago.”
Legend Headwear is based in TriBeCa, lower Manhattan; Jesse can be reached at jesse@ledgeheadwear.com.