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
Malo Lisse America
Regular price £250.00 GBPRegular priceUnit price per£250.00 GBPSale price £250.00 GBP -
Vendor:Paraboot
Michael Grainé Ebène
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Paraboot
Adonis Marron Lis-Cafe
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Sebago
Black Classic Dan Loafer
Regular price £210.00 GBPRegular priceUnit price perSale price £210.00 GBP -
Vendor:Paraboot
Pacific Sandal
Regular price £260.00 GBPRegular priceUnit price per£175.00 GBPSale price £260.00 GBP -
Vendor:The Original Playboy
Dark Brown Chukka Boot
Regular price £270.00 GBPRegular priceUnit price perSale price £270.00 GBP -
Vendor:Astorflex
Dark Chestnut Nuvoflex
Regular price £195.00 GBPRegular priceUnit price per£295.00 GBPSale price £195.00 GBPSale -
Vendor:Sebago
Burgundy Classic Dan Loafer
Regular price £210.00 GBPRegular priceUnit price perSale price £210.00 GBP -
Vendor:The Original Playboy
Black Chukka Boot
Regular price £270.00 GBPRegular priceUnit price perSale price £270.00 GBP -
Vendor:Sebago
Dolphin Waxed Leather Loafer
Regular price £100.00 GBPRegular priceUnit price per£150.00 GBPSale price £100.00 GBPSale -
Vendor:Kleman
Padror Marron
Regular price £160.00 GBPRegular priceUnit price perSale price £160.00 GBP -
Vendor:Astorflex
Dark Chestnut Greenflex Rubber Sole
Regular price £260.00 GBPRegular priceUnit price perSale price £260.00 GBP -
Vendor:Paraboot
Chambord Noir
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Kleman
Padror Noir
Regular price £160.00 GBPRegular priceUnit price per£160.00 GBPSale price £160.00 GBP -
Vendor:Paraboot
Chambord Marron
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Paraboot
Women's Michael Noir
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Paraboot
Avignon Noir
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Sebago
Hurricane Deck Ecru
Regular price £80.00 GBPRegular priceUnit price perSale price £80.00 GBP -
Vendor:Ortigni
Gibsonelli Ivy Grain
Regular price £395.00 GBPRegular priceUnit price perSale price £395.00 GBP -
Vendor:Paraboot
Avignon Marron
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Paraboot
Women's Michael Marron
Regular price £385.00 GBPRegular priceUnit price perSale price £385.00 GBP -
Vendor:Ortigni
Gibsonelli
Regular price £395.00 GBPRegular priceUnit price perSale price £395.00 GBP
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.






































