Jon Gray Handmade Shoes

When you invest in a pair of shoes made by Jon Gray, you are getting soles that, if properly cared for, will last a lifetime. That makes the fact that you may have to wait six months to actually slip them onto your feet seem all right.

Every Jon Gray shoe is made-to-measure; his are elegantly simple brogues made to reflect the personal style of the wearer, and thus require personalized lasts for each client, which Gray then keeps for when the client inevitably comes back for a second pair. After the style and the type of leather are chosen (French calf leather is most commonly used, but he has also made shoes from buffalo and kangaroo), Gray takes a complex series of foot measurements. Each shoe starts as a piece of leather that Gray cuts and stitches, from the sole to the lining. As his work is so customized, Jon Gray’s business is purely a one-man show.

Although clients are excited when the shoe is placed in their hands, they are even more thrilled when the shoes are slipped onto their feet. “The personally designed look of the shoe is the thing that brings clients to my studio, but what brings people back is the way that handmade shoe feels,” says Gray. “There is a tremendous comfort factor. The leather insole is three-eighths of an inch thick, and over time your foot leaves an impression so that it conforms to the shape of your foot, becoming ever-more comfortable. No shoe that you buy in a store is going to feel like this.”

Gray has never worked anywhere other than in shops that custom-make shoes. He was born in 1974, and he started his career by sweeping floors for an orthopedic shoemaker in Dundas, Ontario, while he was still in high school. He apprenticed there before going to work with a theatrical shoemaker in Granville Ferry, a small town in rural Nova Scotia. Gray spent nearly a decade making shoes for on and off Broadway shows, including Wicked, while studying the art of hand-sewn shoes in his spare time.

In 2010, after spending a month in Budapest studying advanced techniques, Gray was energized to do something new and started Jon Gray Handmade Shoes. Operating out of his workshop behind his countryside home in Annapolis Royal, Nova Scotia, hasn’t impeded his clients, who hail internationally. (If customers can’t actually get to meet Gray in person, he offers Skype consultations.)

Jon Gray shoes “are going to evoke a feeling,” he says. And, by utilizing traditional tools and techniques, Jon Gray Handmade Shoes may be a timely construction, yet they are timelessly classic.

Photos by Jillian Wilcox MacAulay.

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