When you think about places you might find hand made men’s shoes, the quaint town of Annapolis Royal probably isn’t the first place that springs to mind. However, located in back of one of the fine old homes just a short stroll from downtown is Jon Gray’s workshop, where for $1000 you can have a beautiful pair of leather shoes custom made to fit your feet perfectly.

Okay, so $1000 may sound crazy expensive for a pair of shoes, and I should add that it will take on average six months for Gray to make them for you, but here’s the thing: These shoes will last you a lifetime, providing that you care for them properly. And these will be your perfect shoe, in the style of your choosing.

Every elegantly simple shoe that Gray creates is made to reflect the personal style of the wearer, as well as be suitable for the life that they lead. Gray’s shoes aren’t trendy; they are timeless classics.

Every shoe is made to measure and requires a pair of lasts to be made for each client, which Gray then keeps aside for when the they comes back for a second pair of shoes (which can then be made for $600, as much of the fitting work has already been done).  

At the initial consult Gray gets to know his client and together they choose a style for the shoe and the type of leather to be used (calfskin is most commonly used, but he has made shoes from buffalo and kangaroo). Then he takes a complex series of measurements, from which he creates the last and then a leather fitting model, which is tried on at the second consultation and then adjusted before the final shoe is made.

Every part of the shoe starts as a piece of leather that Gray cuts and stitches, from the sole to the lining. Because his work is far too specialized for him to let anyone else help, Jon Gray’s business is purely a one man show, which is why clients wait so long to own a pair of his exquisite shoes.

While clients are excited when the shoe is placed in their hands, they are much more so 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 hand made shoes feel. There is a tremendous comfort factor. The leather insole is 3/8 of an inch thick, and over time your foot leaves an impression so that it conforms to the shape of your foot, becoming evermore comfortable,” says Gray. “No shoe that you buy in a store is going to feel like this, partly because of the fit but mostly because of the materials.”

Gray has never worked anywhere other than in shops that custom make shoes: He started out sweeping floors for an orthopedic shoemaker in Ontario while he was still in high-school, then apprenticed from him before going to work with a theatrical shoemaker in the Granville Ferry, in rural Nova Scotia. Gray spent a decade making shoes for Broadway shows like Wicked (which he says gave him a background in pattern making that he couldn’t have got anywhere else), and studying the art of hand sewn shoes in his spare time.

A couple of years ago, Gray decided that he was ready start creating the kind of shoes that he loved. He’d spent a month in Budapest studying advanced techniques, and was energized to do something new and started Jon Gray Handmade Shoes. Being located in the country hasn’t impeded Gray’s business in any way. His clients come from Toronto, Vancouver, Los Angeles and Britain. If they can’t actually get to meet Gray in person, he offers Skype or telephone consultations (and mails them the fitting model).

Gray is always striving to taking things to the next level. Currently, he is finishing up an intricately stitched pair of Norwegian sewn shoes. “It’s a pretty fussy construction, this customer is unlikely to ever to run into another pair,” says Gray, “every time that guy looks down at his shoes, they are going to evoke a feeling.”