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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.

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Sale Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8310)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £143.49

Sale Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(3231)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £120.50

Sale Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(4118)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £114.25

Sale Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(343)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £143.49

Sale Classic Oxford Shoe

Classic Oxford Shoe

(2517)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £143.49

Sale Classic Deck Shoe

Classic Deck Shoe

(747)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £53.88

Sale Classic Cheltenham Brogue - Oxblood

Classic Cheltenham Brogue - Oxblood

(303)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £120.50

Sale Classic Penny Loafer

Classic Penny Loafer

(383)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £114.25

Sale Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(2081)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £114.25

Sale Classic Monk Shoe - Black

Classic Monk Shoe - Black

(2428)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £166.24

Sale Classic Deck Shoe - Navy/Brown

Classic Deck Shoe - Navy/Brown

(121)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £53.88

Sale Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4130)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £120.50

Sale Classic Kempton Shoe

Classic Kempton Shoe

(2644)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £114.25

Sale Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(142)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £143.49

Sale Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

(149)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £120.50

Sale Classic Penny Loafer

Classic Penny Loafer

(955)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £114.25

Sale Classic Monk Brogue - Black

Classic Monk Brogue - Black

(280)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £166.24

Sale Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1781)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £120.50

Sale Classic City Shoe - Black

Classic City Shoe - Black

(2949)

£39.95 £25.00 Save £14.95

Comparable High Street Price: £139.50

Sale Classic Cheltenham Brogue

Classic Cheltenham Brogue

(177)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £120.50

Sale Classic Penny Loafer

Classic Penny Loafer

(2120)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £114.25

Sale Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(64)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £120.50

Sale Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1331)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £120.50

Sale Classic Monk Shoe

Classic Monk Shoe

(1662)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £166.24

Sale Classic Penny Loafer

Classic Penny Loafer

(75)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £114.25

Sale Classic Oxford Shoe

Classic Oxford Shoe

(195)

£39.95 £27.50 Save £12.45

Comparable High Street Price: £143.49

Sale Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(76)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £143.49

Sale Classic Oxford Shoe

Classic Oxford Shoe

(399)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £143.49

Sale Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

(425)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £53.88

Sale Classic Leather Driving Shoe

Classic Leather Driving Shoe

(84)

£39.95 £25.00 Save £14.95

Comparable High Street Price: £78.25

Sale Classic Derby Shoe - Black

Classic Derby Shoe - Black

(39)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £139.50

Sale Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

(370)

£39.95 £27.50 Save £12.45

Comparable High Street Price: £120.50

Sale Classic Lightweight Brogue - Navy

Classic Lightweight Brogue - Navy

(41)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £89.74

Sale Classic Deck Shoe - Blue

Classic Deck Shoe - Blue

(41)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £53.88

Sale Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(142)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £143.49

Sale Classic Deck Shoe - Tobacco

Classic Deck Shoe - Tobacco

(45)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £53.88

Sale Classic Moccasin

Classic Moccasin

(119)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £78.25

Sale Classic Lightweight Brogue - Sand

Classic Lightweight Brogue - Sand

(39)

£39.95 £29.00 Save £10.95

Comparable High Street Price: £89.74

Sale Classic Driving Shoe

Classic Driving Shoe

(109)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £78.25

Sale Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(6)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £139.50

Sale Classic Slip-On Deck Shoe - Navy/Brown

Classic Slip-On Deck Shoe - Navy/Brown

(425)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £53.88

Sale Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(11)

£42.50 £35.00 Save £7.50

Comparable High Street Price: £139.50

Sale Classic Slip-On Deck Shoe - Camel

Classic Slip-On Deck Shoe - Camel

(425)

£39.95 £35.00 Save £4.95

Comparable High Street Price: £53.88

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