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:Rancourt & Co.
Chocolate Beefroll Grain Leather Loafers
Regular price £295.00 GBPRegular priceUnit price per£420.00 GBPSale price £295.00 GBPSale -
Vendor:Rancourt & Co.
Burgundy Pinch Penny Calf Leather Loafers
Regular price £295.00 GBPRegular priceUnit price per£420.00 GBPSale price £295.00 GBPSale -
Vendor:Rancourt & Co.
Black Pinch Penny Calf Leather Loafers
Regular price £295.00 GBPRegular priceUnit price per£420.00 GBPSale price £295.00 GBPSale -
Vendor:Rancourt & Co.
Black Horse Bit Calf Leather Loafers
Regular price £295.00 GBPRegular priceUnit price per£450.00 GBPSale price £295.00 GBPSale -
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 £270.00 GBPRegular priceUnit price per£320.00 GBPSale price £270.00 GBPSale -
Vendor:The Original Playboy
x Steve McQueen Black Chukka Boot
Regular price £270.00 GBPRegular priceUnit price per£320.00 GBPSale price £270.00 GBPSale -
Sold outVendor:D. LeporiWomen's Burgundy College Man Loafers
Regular price £135.00 GBPRegular priceUnit price per£195.00 GBPSale price £135.00 GBPSold out -
Vendor:D. Lepori
Burgundy College Man Loafers
Regular price £135.00 GBPRegular priceUnit price per£195.00 GBPSale price £135.00 GBPSale -
Sold outVendor:D. LeporiBlack College Man Loafers
Regular price £135.00 GBPRegular priceUnit price per£195.00 GBPSale price £135.00 GBPSold out -
SaleVendor:AstorflexMattone Sadelflex
Regular price £135.00 GBPRegular priceUnit price per£225.00 GBPSale price £135.00 GBPSale -
SaleVendor:AstorflexEcru Sadelflex
Regular price £120.00 GBPRegular priceUnit price per£225.00 GBPSale price £120.00 GBPSale -
Vendor:Astorflex
Dark Chestnut Nuvoflex
Regular price £295.00 GBPRegular priceUnit price per£295.00 GBPSale price £295.00 GBP -
Vendor:Astorflex
Dark Chestnut Greenflex Rubber Sole
Regular price £260.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Chambord Marron
Regular price £385.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Chambord Noir
Regular price £385.00 GBPRegular priceUnit price per -
SaleVendor:ParabootArles Whiskey Suede
Regular price £250.00 GBPRegular priceUnit price per£385.00 GBPSale price £250.00 GBPSale -
Vendor:Paraboot
Arles Lisse Ecorce
Regular price £385.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Avignon Noir
Regular price £385.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Avignon Marron
Regular price £385.00 GBPRegular priceUnit price per -
Vendor:Paraboot
Women's Michael Marron
Regular price £385.00 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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John Simons/Since 1955 Book Signing and Launch ...
Bebop meets books. What a fantastic night at 46 Chiltern Street. A big thank you to everyone who joined us for our signing event on 6th November 2025. It was...
John Simons/Since 1955 Book Signing and Launch ...
Bebop meets books. What a fantastic night at 46 Chiltern Street. A big thank you to everyone who joined us for our signing event on 6th November 2025. It was...
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Customer Spotlight: Adam Soffe
In this Customer Spotlight, we introduce Adam Soffe. Based in London, his life revolves around music, family, sport and style. He’s a father of two young boys and, by day,...
Customer Spotlight: Adam Soffe
In this Customer Spotlight, we introduce Adam Soffe. Based in London, his life revolves around music, family, sport and style. He’s a father of two young boys and, by day,...
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Customer Spotlight: Shirley Au
After years in the fast-paced agency world, Shirley finds it rewarding to be part of a business where craftmanship, quality, and sustainability set the pace. We spoke with Shirley to...
Customer Spotlight: Shirley Au
After years in the fast-paced agency world, Shirley finds it rewarding to be part of a business where craftmanship, quality, and sustainability set the pace. We spoke with Shirley to...
