Classic Shoes

Here at Samuel Windsor, our collection of men's classic shoes features footwear made only from premium grade leather and suede. Constructed using traditional methods, our classic collection offers a comfortable shoe for every occasion – from formal men's Oxford shoes through to relaxed boat shoes for the weekend.

Any 2 Pairs for £75

Classic Oxford Shoe - Black

(8301)

£39.95

Comparable High Street Price: £143.49

Any 2 Pairs for £75

Classic Cheltenham Brogue - Black

(3226)

£39.95

Comparable High Street Price: £120.50

Any 2 Pairs for £75

Classic Penny Loafer Shoe - Black

(4116)

£42.50

Comparable High Street Price: £129.75

Any 2 Pairs for £75

Classic Oxford Shoe - Oxblood

(340)

£39.95

Comparable High Street Price: £143.49

Any 2 Pairs for £75

Classic Oxford Shoe

(2514)

£39.95

Comparable High Street Price: £143.49

Any 2 Pairs for £75

Classic Cheltenham Brogue - Oxblood

(296)

£39.95

Comparable High Street Price: £120.50

Any 2 Pairs for £75

Classic Deck Shoe

(743)

£39.95

Comparable High Street Price: £76.49

Any 2 Pairs for £75

Classic Penny Loafer

(380)

£42.50

Comparable High Street Price: £129.75

Any 2 Pairs for £75

Classic Kempton Shoe - Black

(2079)

£42.50

Comparable High Street Price: £129.75

Any 2 Pairs for £75

Classic Monk Shoe - Black

(2427)

£39.95

Comparable High Street Price: £163.74

Any 2 Pairs for £75

Classic Semi-Brogue - Black

(4129)

£39.95

Comparable High Street Price: £120.50

Any 2 Pairs for £75

Classic Chichester Shoe - Black

(138)

£39.95

Comparable High Street Price: £143.49

Any 2 Pairs for £75

Classic Kempton Shoe

(2640)

£42.50

Comparable High Street Price: £129.75

Any 2 Pairs for £75

Classic Cheltenham Brogue in Suede

(149)

£39.95

Comparable High Street Price: £120.50

Any 2 Pairs for £75

Classic Deck Shoe - Navy/Brown

(119)

£39.95

Comparable High Street Price: £76.49

Any 2 Pairs for £75

Classic Monk Brogue - Black

(279)

£39.95

Comparable High Street Price: £163.74

Any 2 Pairs for £75

Classic Penny Loafer

(955)

£42.50

Comparable High Street Price: £129.75

Sale

Classic Semi-Brogue

(1695)

~~£39.95~~ £27.50 Save £12.45

Comparable High Street Price: £120.50

Any 2 Pairs for £75

Classic Quarter-Brogue - Black

(1778)

£39.95

Comparable High Street Price: £120.50

Any 2 Pairs for £75

Classic Cheltenham Brogue

(176)

£39.95

Comparable High Street Price: £120.50

Sale

Classic City Shoe - Black

(2946)

~~£39.95~~ £25.00 Save £14.95

Comparable High Street Price: £139.50

Any 2 Pairs for £75

Classic Penny Loafer

(2119)

£42.50

Comparable High Street Price: £129.75

Any 2 Pairs for £75

Classic Cheltenham Brogue In Suede - Mid Brown

(61)

£39.95

Comparable High Street Price: £120.50

Any 2 Pairs for £75

Classic Sandhurst Shoe

(1329)

£39.95

Comparable High Street Price: £120.50

Sale

Classic Oxford Shoe

(195)

~~£39.95~~ £27.50 Save £12.45

Comparable High Street Price: £143.49

Any 2 Pairs for £75

Classic Penny Loafer

(75)

£42.50

Comparable High Street Price: £129.75

Any 2 Pairs for £75

Classic Monk Shoe

(1659)

£39.95

Comparable High Street Price: £163.74

Any 2 Pairs for £75

Classic Oxford Shoe

(396)

£39.95

Comparable High Street Price: £143.49

Any 2 Pairs for £75

Classic Suede Oxford Shoe

(76)

£39.95

Comparable High Street Price: £143.49

Sale

Classic Durham Shoe - Black

(150)

~~£39.95~~ £25.00 Save £14.95

Comparable High Street Price: £120.50

Sale

Classic Sandhurst Shoe - Black

(370)

~~£39.95~~ £27.50 Save £12.45

Comparable High Street Price: £120.50

Any 2 Pairs for £75

Classic Slip-On Deck Shoe

(422)

£39.95

Comparable High Street Price: £76.49

Any 2 Pairs for £75

Classic Lightweight Brogue - Navy

(38)

£39.95

Comparable High Street Price: £79.99

Any 2 Pairs for £75

Classic Derby Shoe - Black

(36)

£42.50

Comparable High Street Price: £139.50

Any 2 Pairs for £75

Classic Deck Shoe - Blue

(40)

£39.95

Comparable High Street Price: £76.49

Sale

Classic Leather Driving Shoe

(82)

~~£39.95~~ £25.00 Save £14.95

Comparable High Street Price: £74.30

Sale

Classic Moccasin - Brown

(38)

~~£39.95~~ £25.00 Save £14.95

Comparable High Street Price: £74.30

Any 2 Pairs for £75

Classic Deck Shoe - Tobacco

(44)

£39.95

Comparable High Street Price: £76.49

Any 2 Pairs for £75

Classic Moccasin

(118)

£39.95

Comparable High Street Price: £74.30

Any 2 Pairs for £75

Classic Chichester Shoe - Oxblood

(138)

£39.95

Comparable High Street Price: £143.49

Sale

Classic Lightweight Brogue - Sand

(35)

~~£39.95~~ £29.00 Save £10.95

Comparable High Street Price: £79.99

Any 2 Pairs for £75

Classic Driving Shoe

(109)

£39.95

Comparable High Street Price: £74.30

Any 2 Pairs for £75

Classic Derby Shoe - Suede

(5)

£42.50

Comparable High Street Price: £139.50

Any 2 Pairs for £75

Classic Derby Shoe - Black Suede

(9)

£42.50

Comparable High Street Price: £139.50

Any 2 Pairs for £75

Classic Slip-On Deck Shoe - Navy/Brown

(422)

£39.95

Comparable High Street Price: £76.49

Any 2 Pairs for £75

Classic Slip-On Deck Shoe - Camel

(422)

£39.95

Comparable High Street Price: £76.49

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