Bespoke Shoes Chicago
Canons Trunk Show
Chicago Trunk Show
We are next in Chicago on October 29th & 30th 2026 for our Fall Trunk Show. We visit three times a year, staying in the Peninsula Hotel.
Appointments are held individually with our Lastmaker, Simon Bolzoni, in a private hotel suite. Each consultation lasts approximately one hour and includes an assessment of your feet, measurements and a discussion of your fitting requirements, preferred styles and leathers. Clients are also welcome to examine selected examples from our historic archive, together with our range of leathers, including hand-coloured calfskins. Appointments must be arranged in advance.
Peninsula Hotel
108 East Superior Street (at North Michigan Avenue), Chicago, Illinois 60611
Located along the ‘Magnificent Mile’ in downtown Chicago, the Peninsula Hotel is an elegant and light-filled sanctuary from which to host our bespoke customers. We have been staying here for over 7 years, and always appreciate the attention to detail and quietly professional service that set this hotel apart.
Why Canons bespoke?
• London bespoke shoemakers since 1840
• Individual hand-carved beechwood lasts
• Lasts developed for different styles and fitting requirements
• Our own asymmetrical pattern-cutting technique
• Trial fittings whenever new lasts are made
• Traditional English hand-welted construction
• Entirely handmade bespoke shoes and boots
• Specialist skills refined over generations
• Hand finishing at our London workshop
• Personal lasts and patterns retained for future commissions
Simon Bolzoni
Lastmaker & Managing Director of Canons
Simon began his training in last-making in 2006 under Terry Moore, London’s pre-eminent bespoke lastmaker. Building upon this traditional foundation, he has continued to develop Canons’ own methods of individual last-making and pattern cutting. His approach combines an understanding of each client’s fitting requirements with careful consideration of the proportions and character of each shoe.
Recent Bespoke Examples
Customer Testimonials
“Among the finest shoe craftsmen in the world. Canons bespoke shoes are the most comfortable and durable that I have ever purchased.”
Chris O
“The shoes they have made for me are the result of their fastidiously detailed approach to their craft, knowledge, creative expression and ultimately my comfort.”
Paul C
“I have tried a number of bespoke shoemakers in London and only Canons have succeeded in making shoes that fit me and look great.”
Charles C