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All Leather Shoes

Handmade by master craftsmen, our men's leather shoes are comfortable, stylish, and designed to last. Whether you're looking for a pair of polished black Oxford shoes to wear with a suit, or a relaxed pair of brown brogues, good quality leather shoes from Samuel Windsor are a sound investment.

2 for £75

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£39.95

Typical High Street Price: £134.74

2 for £75

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

£39.95

Typical High Street Price: £134.74

2 for £75

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£39.95

Typical High Street Price: £124.33

2 for £75

Classic Penny Loafer

Classic Penny Loafer

£39.95

Typical High Street Price: £124.33

2 for £75

Classic Monk Shoe - Black

Classic Monk Shoe - Black

£39.95

Typical High Street Price: £124.33

2 for £75

Classic Cheltenham Brogue

Classic Cheltenham Brogue

£39.95

Typical High Street Price: £125.99

Prestige Whitworth Brogue

£49.50

Typical High Street Price: £161.65

Prestige Chelsea Boot - Black

£49.95

Typical High Street Price: £183.00

2 for £75

Classic Kempton Shoe

Classic Kempton Shoe

£39.95

Typical High Street Price: £124.33

2 for £75

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£39.95

Typical High Street Price: £124.33

2 for £75

Classic Deck Shoe

Classic Deck Shoe

£39.95

Typical High Street Price: £94.75

2 for £75

Classic Oxford Shoe

Classic Oxford Shoe

£39.95

Typical High Street Price: £134.74

Prestige Chelsea Boot

£49.95

Typical High Street Price: £183.00

2 for £75

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£39.95

Typical High Street Price: £125.99

Prestige Oxford Shoe - Rubber Sole - Black

£52.50

Typical High Street Price: £129.98

2 for £75

Classic Semi-Brogue

Classic Semi-Brogue

£39.95

Typical High Street Price: £125.99

Prestige Twin Monk Shoe - Oxblood

£47.95

Typical High Street Price: £124.33

2 for £75

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£39.95

Typical High Street Price: £125.99

2 for £75

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

£39.95

Typical High Street Price: £134.74

2 for £75

Classic Deck Shoe - Navy/Brown

Classic Deck Shoe - Navy/Brown

£39.95

Typical High Street Price: £94.75

2 for £75

Classic City Shoe - Black

Classic City Shoe - Black

£39.95

Typical High Street Price: £129.98

2 for £75

Classic Monk Shoe

Classic Monk Shoe

£39.95

Typical High Street Price: £124.33

Prestige Bartlett Brogue

£52.50

Typical High Street Price: £129.98

Prestige Cumbria Boot

£49.50

Typical High Street Price: £92.50

2 for £75

Classic Penny Loafer

Classic Penny Loafer

£39.95

Typical High Street Price: £124.33

2 for £75

Classic Penny Loafer

Classic Penny Loafer

£39.95

Typical High Street Price: £124.33

Prestige Dress Shoe - Black

£47.95

Typical High Street Price: £114.75

Prestige Oxford Dress Shoe - Black

£47.95

Typical High Street Price: £114.75

2 for £75

Classic Penny Loafer

Classic Penny Loafer

£39.95

Typical High Street Price: £124.33

2 for £75

Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£39.95

Typical High Street Price: £94.75

2 for £75

Classic Durham Shoe - Black

Classic Durham Shoe - Black

£39.95

Typical High Street Price: £125.99

2 for £75

Classic Oxford Shoe

Classic Oxford Shoe

£39.95

Typical High Street Price: £134.74

Prestige Oxford Shoe - Black

£47.95

Typical High Street Price: £134.74

Prestige Whitworth Brogue - Black

£49.50

Typical High Street Price: £161.65

Prestige Slip-On Deck Shoe

£47.95

Typical High Street Price: £119.99

Classic Deck Shoe - Blue

£26.50

Typical High Street Price: £94.75

Prestige Leather Lace-Up Deck Shoe

£47.95

Typical High Street Price: £119.99

Prestige Semi-Brogue

£47.95

Typical High Street Price: £125.99

Prestige Deck Shoe

£47.95

Typical High Street Price: £119.99

Prestige Tasselled Loafer - Black

£47.95

Typical High Street Price: £124.33

Prestige Split Brogue

£49.50

Typical High Street Price: £161.65

Classic Deck Shoe - Tobacco

£26.50

Typical High Street Price: £94.75

Prestige Slip-On Deck Shoe

£47.95

Typical High Street Price: £119.99

Prestige Lace-Up Deck Shoe

£47.95

Typical High Street Price: £119.99

Prestige Oxford Shoe - Rubber Sole

£52.50

Typical High Street Price: £129.98

Prestige Lightweight Derby - Tan

£47.95

Typical High Street Price: £93.32

Classic Monk Shoe

£28.95

Typical High Street Price: £124.33

Prestige Bartlett Brogue

£37.95

Typical High Street Price: £129.98