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:Paraboot
Michael Noir
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Paraboot
Michael Marron
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Paraboot
Avoriaz Écorce
Regular price £429.00 GBPRegular priceUnit price perSale price £429.00 GBP -
Vendor:Paraboot
Clusaz Écorce
Regular price £395.00 GBPRegular priceUnit price perSale price £395.00 GBP -
Vendor:Paraboot
Clusaz Noir
Regular price £395.00 GBPRegular priceUnit price perSale price £395.00 GBP -
Vendor:The Original Playboy
Taupe Suede Chukka Boot
Regular price £270.00 GBPRegular priceUnit price perSale price £270.00 GBP -
Vendor:Paraboot
Women's Orsay Noir
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Astorflex
Dark Chestnut Greenflex
Regular price £205.00 GBPRegular priceUnit price perSale price £205.00 GBP -
Vendor:Astorflex
Whiskey Greenflex
Regular price £205.00 GBPRegular priceUnit price perSale price £205.00 GBP -
Vendor:Astorflex
Stone Greenflex
Regular price £205.00 GBPRegular priceUnit price perSale price £205.00 GBP -
Vendor:The Original Playboy
Burgundy Dallas Polido Leather Loafer
Regular price £180.00 GBPRegular priceUnit price perSale price £180.00 GBP -
Vendor:The Original Playboy
Black Dallas Polido Leather Loafer
Regular price £180.00 GBPRegular priceUnit price perSale price £180.00 GBP -
Vendor:The Original Playboy
Brown 64 Chukka Boot
Regular price £270.00 GBPRegular priceUnit price perSale price £270.00 GBP -
Vendor:The Original Playboy
Black 64 Chukka Boot
Regular price £270.00 GBPRegular priceUnit price perSale price £270.00 GBP -
Vendor:Paraboot
Adonis Marron Lis-Cafe
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Kleman
Padror Marron
Regular price £160.00 GBPRegular priceUnit price perSale price £160.00 GBP -
Vendor:Kleman
Padror Noir
Regular price £160.00 GBPRegular priceUnit price per£160.00 GBPSale price £160.00 GBP -
Vendor:Ortigni
Gibsonelli Ivy Grain
Regular price £395.00 GBPRegular priceUnit price perSale price £395.00 GBP -
Vendor:Paraboot
Michael Grainé Ebène
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Sebago
Burgundy Classic Dan Loafer
Regular price £210.00 GBPRegular priceUnit price perSale price £210.00 GBP -
Vendor:Sebago
Black Classic Dan Loafer
Regular price £210.00 GBPRegular priceUnit price perSale price £210.00 GBP -
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
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.





































