Classic Shoes

Classic Derby Shoe - Suede

£42.50 Was £100.00

Any 2 for £70

This practical whole cut derby shoe is a perfect addition to our Classic Collection.

Classic Derby Shoe - Black Suede

£42.50 Was £100.00

Any 2 for £70

This practical whole cut derby shoe is a perfect addition to our Classic Collection.

Classic Chichester Shoe - Oxblood

£39.95 Was £100.00

Any 2 for £70

A traditional Oxford with a modern twist, they feature sleek polished quarters and definitive basket weave design to the vamp quarter.

Classic Slip-On Deck Shoe - Navy/Brown

£37.95 Was £100.00

Buy 2 pairs for £70

The Classic collection wouldn’t be complete without these wonderful men’s leather deck shoes.

Classic Semi-Brogue - Black

£39.95 Was £100.00

Any 2 for £70

Classic Semi-Brogues, designed by craftsmen at Samuel Windsor, allow the foot to flex in its most natural way, ensuring maximum comfort.

Classic Oxford Shoe - Black

£39.95 Was £100.00

Any 2 for £70

Oxford Shoes have been designed using time honoured shoe making techniques. These handmade five-eyelet Men's Classic Oxford Shoes, with sleek polished quarters and a definitive cap toe, are a gentleman's classic.

Classic Monk Shoe - Black

£39.95 Was £100.00

Any 2 for £70

Classic Monk Shoes are another traditional classic from Samuel Windsor. Intricately constructed from over 50 natural components; from the polished leather sole to the full leather lining.

Classic Monk Shoe

£39.95 Was £100.00

Any 2 for £70

Classic Monk Shoes are another traditional classic from Samuel Windsor.

Classic Sandhurst Shoe - Black

£37.95 Was £100.00

Save £62.05

Classic Sandhurst Shoes will serve you for many years to come.

Classic Penny Loafer

£42.50 Was £100.00

Any 2 for £70

Classic Penny Loafers are classic formal shoes combined with supple easy slip on access.

Classic Oxford Shoe

£39.95 Was £100.00

Any 2 For £70

Classic Oxford Shoes, online from Samuel Windsor. Tailored quality at outstanding prices.

Classic Slip-On Boat Shoe

£39.95 Was £100.00

Any 2 For £70

Classic Slip-On Boat Shoe, timeless, sophisticated, understated yet coolly confident – they will never go out of style.

Classic Moccasin

£39.95 Was £100.00

Buy 2 Pairs for £75

Made from the finest, soft Italian leather, our Classic moccasins are carefully hand stitched, creating a wonderfully comfortable and durable casual shoe.

Classic Monk Brogue - Black

£39.95 Was £100.00

Any 2 for £70

Handmade using a Goodyear Welted construction, this monk brogue shoes have been produced using the finest Italian leather uppers which offer an unbeatable combination of comfort and durability representing outstanding quality at an exceptional price.

Classic Cheltenham Brogue

£37.95 Was £100.00

Buy 2 pairs for £70

Cheltenham Half Brogues mens leather shoes, formal shoes or office shoes, mens brogue shoes which retain the elegant craftmanship personified by hand-stitching.

Classic Oxford Shoe - Oxblood

£39.95 Was £100.00

Any 2 for £70

Classic Oxford Shoes, online from Samuel Windsor. Tailored quality at outstanding prices.

Classic Cheltenham Brogue

£39.95 Was £100.00

Any 2 for £70

Buy classic black brogues from Samuel Windsor. Our handmade brogues offer Goodyear welted construction for long lasting quality. Visit now for great offers.

Classic Suede Oxford Shoe

£39.95 Was £100.00

Buy 2 pairs for £70

Classic Suede Oxford Shoes in black from Samuel Windsor. Visit now for outstanding quality and fantastic offers.

Classic Deck Shoe - Blue

£39.95 Was £100.00

Any 2 for £70

Classic Deck Shoe from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

Classic Leather Driving Shoe

£37.95 Was £100.00

Save £62.05

Classic Driving Shoe are comfortable to wear which is perfect for the summer.

Classic Lightweight Brogue - Navy

£37.95 Was £115.00

Buy 2 pairs for £70

These Lightweight Classic Collection summer shoes feature an exceptionally light and comfortable sole

Classic Lightweight Brogue - Sand

£37.95 Was £115.00

Buy 2 pairs for £70

These Lightweight Classic Collection summer shoes feature an exceptionally light and comfortable sole

Classic Chichester Shoe - Black

£39.95 Was £100.00

Any 2 for £70

Made using time honoured shoemaking techniques, these handmade five-eyelet Classic Oxford shoes are a traditional Oxford with a modern twist.

Classic Penny Loafer Shoe - Black

£42.50 Was £100.00

Any 2 for £70

Classic Penny Loafer Shoe, are a handmade classic dress style combined with easy slip-on access. The Penny Loafer Shoe's accommodating leather upper has been handcrafted, raising it to the highest level of shoe quality.

Classic Oxford Shoe

£39.95 Was £100.00

Any 2 for £70

Using time honoured shoe making techniques, these handmade five-eyelet Classic Oxford Shoes with sleek polished quarters and a definitive cap toe, are a gentleman's classic.

Classic Lace Shoe - Brown

£39.95

Men's Classic Brown Lace-up Shoes are a traditional men's footwear option and have been handcrafted for a premium look and unrivalled comfort. Part of an extensive selection of Men's Footwear, now available at Mail Shop.

Classic Cheltenham Brogue - Black

£39.95 Was £100.00

Any 2 for £70

Classic Cheltenham Brogues retain the elegant craftsmanship personified by hand-stitching and make a very smart and highly traditional pair of Men's Shoes.

Classic Kempton Shoe - Black

£42.50 Was £100.00

Any 2 for £70

Classic Kempton Slip-On Shoes are designed to look as good as formal shoes, office shoes or with casual wear.

Classic Penny Loafer

£42.50 Was £100.00

Any 2 for £70

Classic Penny Loafer, are a handmade classic dress style combined with easy slip-on access. The Penny Loafer Shoe's accommodating leather upper has been handcrafted, raising it to the highest level of shoe quality. The Goodyear