Since the days of The Squire Shop, our shoe collection has always been a focal point at John Simons. Explore our range of Ivy League classics, including suede chukka boots from Astorflex and Original Playboy, iconic penny and beefroll loafers by Rancourt, and robust workwear options from Paraboot, as well as much more. Our collection ensures you’ll step out in 4/4 style, wherever your journey takes you.
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Vendor:Kleman
Padror Marron
Regular price £160.00 GBPRegular priceUnit price per -
Vendor:Kleman
Padror Noir
Regular price £160.00 GBPRegular priceUnit price per -
Vendor:Ortigni
Gibsonelli Ivy Grain
Regular price £395.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Michael Grainé Ebène
Regular price £385.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Lisse América Yosemite Boot
Regular price £285.00 GBPRegular priceUnit price per -
Vendor:Sebago
Burgundy Classic Dan Loafer
Regular price £210.00 GBPRegular priceUnit price per -
Vendor:Sebago
Black Classic Dan Loafer
Regular price £210.00 GBPRegular priceUnit price per -
Vendor:Rancourt & Co.
Chocolate Beefroll Grain Leather Loafers
Regular price £420.00 GBPRegular priceUnit price per -
Vendor:Rancourt & Co.
Burgundy Pinch Penny Calf Leather Loafers
Regular price £420.00 GBPRegular priceUnit price per -
Vendor:Rancourt & Co.
Black Pinch Penny Calf Leather Loafers
Regular price £420.00 GBPRegular priceUnit price per -
Vendor:Rancourt & Co.
Black Horse Bit Calf Leather Loafers
Regular price £450.00 GBPRegular priceUnit price per -
Vendor:The Original Playboy
Black Chukka Shoe
Regular price £250.00 GBPRegular priceUnit price per -
Vendor:The Original Playboy
Dark Brown Chukka Boot
Regular price £270.00 GBPRegular priceUnit price per -
Vendor:The Original Playboy
Black Chukka Boot
Regular price £270.00 GBPRegular priceUnit price per -
Vendor:The Original Playboy
x Steve McQueen Bullitt Cognac Chukka Boot
Regular price £320.00 GBPRegular priceUnit price per -
Vendor:The Original Playboy
x Steve McQueen Dark Brown Chukka Boot
Regular price £320.00 GBPRegular priceUnit price per -
Vendor:The Original Playboy
x Steve McQueen Black Chukka Boot
Regular price £320.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Marron Moyen Shoe Cream Polish–Light Brown
Regular price £10.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Marron Fonce Shoe Cream Polish–Dark Brown
Regular price £10.00 GBPRegular priceUnit price per -
Sold outVendor:ParabootNoir Shoe Cream Polish
Regular price £10.00 GBPRegular priceUnit price per -
Vendor:D. Lepori
Women's Black College Man Loafers
Regular price £195.00 GBPRegular priceUnit price per -
Vendor:D. Lepori
Women's Burgundy College Man Loafers
Regular price £195.00 GBPRegular priceUnit price per -
Vendor:D. Lepori
Burgundy College Man Loafers
Regular price £195.00 GBPRegular priceUnit price per -
Vendor:D. Lepori
Black College Man Loafers
Regular price £195.00 GBPRegular priceUnit price per
VINTAGE COLLECTION
Selected vintage, deadstock and one-off pieces curated through the discerning eye of John Simons. From classic Ivy League pieces of yesteryear to exquisite British tailoring, shop our one-off items and stand out from the crowd.
Journal
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Customer Spotlight: Peter Robinson
In this Customer Spotlight, we explore the life and experiences of Peter Robinson, an esteemed photographer deeply connected to British fashion and style. Born in February 1944 and educated at...
Customer Spotlight: Peter Robinson
In this Customer Spotlight, we explore the life and experiences of Peter Robinson, an esteemed photographer deeply connected to British fashion and style. Born in February 1944 and educated at...
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Customer Spotlight: Aya Burns
In this Customer Spotlight, we introduce Aya Burns—a designer whose deep appreciation for timeless style and quality craftsmanship shapes her every purchase and sartorial philosophy. Aya’s journey began as a...
Customer Spotlight: Aya Burns
In this Customer Spotlight, we introduce Aya Burns—a designer whose deep appreciation for timeless style and quality craftsmanship shapes her every purchase and sartorial philosophy. Aya’s journey began as a...
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The Original Playboy X Steve McQueen
The story of The Original Playboy shoes began in 1936 when English shoemaker Hutton in Northampton created a completely new shoe with a unique and patented crepe sole construction. The ‘Play-Boy’, as...
The Original Playboy X Steve McQueen
The story of The Original Playboy shoes began in 1936 when English shoemaker Hutton in Northampton created a completely new shoe with a unique and patented crepe sole construction. The ‘Play-Boy’, as...
