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Classic Shoes

Samuel Windsor Classic shoes are made with premium grade leather, using traditional methods and construction. Our classic shoe collection includes timeless styles from formal men's Oxford shoes to more bohemian suede brogues. If you're looking for a classic boot, you'll find a pair of men's Chelsea boots the perfect fit.

Sale

2 for £70

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(7369)

£39.95 £37.50 Save £2.45

Typical High Street Price: £132.49

Sale

2 for £70

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(2828)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(3710)

£39.95 £37.50 Save £2.45

Typical High Street Price: £124.33

Sale

2 for £70

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(164)

£39.95 £37.50 Save £2.45

Typical High Street Price: £132.49

Sale

2 for £70

Classic Oxford Shoe

Classic Oxford Shoe

(2229)

£39.95 £37.50 Save £2.45

Typical High Street Price: £132.49

Sale

2 for £70

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(3746)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Cheltenham Brogue

Classic Cheltenham Brogue

(149)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Penny Loafer

Classic Penny Loafer

(330)

£39.95 £37.50 Save £2.45

Typical High Street Price: £124.33

Sale

2 for £70

Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

(95)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Monk Shoe - Black

Classic Monk Shoe - Black

(2110)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.07

Sale

2 for £70

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(22)

£39.95 £37.50 Save £2.45

Typical High Street Price: £132.49

Sale

2 for £70

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(1845)

£39.95 £37.50 Save £2.45

Typical High Street Price: £124.33

Sale

2 for £70

Classic Deck Shoe

Classic Deck Shoe

(627)

£39.95 £37.50 Save £2.45

Typical High Street Price: £91.75

Sale

2 for £70

Classic Kempton Shoe

Classic Kempton Shoe

(2282)

£39.95 £37.50 Save £2.45

Typical High Street Price: £124.33

Sale

2 for £70

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1617)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Semi-Brogue

Classic Semi-Brogue

(1524)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Penny Loafer

Classic Penny Loafer

(876)

£39.95 £37.50 Save £2.45

Typical High Street Price: £124.33

Sale

2 for £70

Classic Monk Brogue - Black

Classic Monk Brogue - Black

(195)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.07

Sale

2 for £70

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1205)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Penny Loafer

Classic Penny Loafer

(1911)

£39.95 £37.50 Save £2.45

Typical High Street Price: £124.33

Sale

2 for £70

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(49)

£39.95 £37.50 Save £2.45

Typical High Street Price: £132.49

Sale

2 for £70

Classic Cheltenham Brogue

Classic Cheltenham Brogue

(116)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic City Shoe - Black

Classic City Shoe - Black

(2678)

£39.95 £37.50 Save £2.45

Typical High Street Price: £123.32

Sale

2 for £70

Classic Monk Shoe

Classic Monk Shoe

(1439)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.07

Sale

2 for £70

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(20)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Penny Loafer

Classic Penny Loafer

(33)

£39.95 £37.50 Save £2.45

Typical High Street Price: £124.33

Sale

2 for £70

Classic Durham Shoe - Black

Classic Durham Shoe - Black

(95)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Sale

2 for £70

Classic Oxford Shoe

Classic Oxford Shoe

(145)

£39.95 £37.50 Save £2.45

Typical High Street Price: £132.49

Sale

2 for £70

Classic Deck Shoe - Navy/Brown

Classic Deck Shoe - Navy/Brown

(49)

£39.95 £37.50 Save £2.45

Typical High Street Price: £91.75

Sale

2 for £70

Classic Oxford Shoe

Classic Oxford Shoe

(319)

£39.95 £37.50 Save £2.45

Typical High Street Price: £132.49

Sale

2 for £70

Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

(361)

£39.95 £37.50 Save £2.45

Typical High Street Price: £91.75

Classic Deck Shoe - Blue

(17)

£26.50

Typical High Street Price: £91.75

Sale

2 for £70

Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

(319)

£39.95 £37.50 Save £2.45

Typical High Street Price: £125.99

Classic Moccasin

(86)

£25.50

Typical High Street Price: £77.99

Classic Moccasin - Brown

(18)

£25.50

Typical High Street Price: £77.99

Classic Deck Shoe - Tobacco

(21)

£26.50

Typical High Street Price: £91.75

Classic Driving Shoe

(37)

£25.50

Typical High Street Price: £77.99

Classic Driving Shoe

(87)

£25.50

Typical High Street Price: £77.99

Classic Monk Shoe

(23)

£28.95

Typical High Street Price: £125.07