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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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    Any 2 Pairs for £75

    Classic Oxford Shoe - Black

    Classic Oxford Shoe - Black

    (8310)

    £39.95

    Comparable High Street Price: £133.49

    Any 2 Pairs for £75

    Classic Cheltenham Brogue - Black

    Classic Cheltenham Brogue - Black

    (3231)

    £39.95

    Comparable High Street Price: £120.50

    Any 2 Pairs for £75

    Classic Penny Loafer Shoe - Black

    Classic Penny Loafer Shoe - Black

    (4119)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £112.00

    Any 2 Pairs for £75

    Classic Oxford Shoe - Oxblood

    Classic Oxford Shoe - Oxblood

    (343)

    £39.95

    Comparable High Street Price: £133.49

    Any 2 Pairs for £75

    Classic Oxford Shoe

    Classic Oxford Shoe

    (2518)

    £39.95

    Comparable High Street Price: £133.49

    Any 2 Pairs for £75

    Classic Deck Shoe

    Classic Deck Shoe

    (747)

    £39.95

    Comparable High Street Price: £73.99

    Any 2 Pairs for £75

    Classic Cheltenham Brogue - Oxblood

    Classic Cheltenham Brogue - Oxblood

    (303)

    £39.95

    Comparable High Street Price: £120.50

    Any 2 Pairs for £75

    Classic Penny Loafer

    Classic Penny Loafer

    (383)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £112.00

    Any 2 Pairs for £75

    Classic Kempton Shoe - Black

    Classic Kempton Shoe - Black

    (2081)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £112.00

    Any 2 Pairs for £75

    Classic Monk Shoe - Black

    Classic Monk Shoe - Black

    (2428)

    £39.95

    Comparable High Street Price: £154.99

    Any 2 Pairs for £75

    Classic Semi-Brogue - Black

    Classic Semi-Brogue - Black

    (4130)

    £39.95

    Comparable High Street Price: £120.50

    Any 2 Pairs for £75

    Classic Kempton Shoe

    Classic Kempton Shoe

    (2644)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £112.00

    Any 2 Pairs for £75

    Classic Chichester Shoe - Black

    Classic Chichester Shoe - Black

    (142)

    £39.95

    Comparable High Street Price: £133.49

    Any 2 Pairs for £75

    Classic Deck Shoe - Navy/Brown

    Classic Deck Shoe - Navy/Brown

    (121)

    £39.95

    Comparable High Street Price: £73.99

    Any 2 Pairs for £75

    Classic Cheltenham Brogue in Suede

    Classic Cheltenham Brogue in Suede

    (149)

    £39.95

    Comparable High Street Price: £120.50

    Any 2 Pairs for £75

    Classic Penny Loafer

    Classic Penny Loafer

    (955)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £112.00

    Any 2 Pairs for £75

    Classic Monk Brogue - Black

    Classic Monk Brogue - Black

    (280)

    £39.95

    Comparable High Street Price: £154.99

    Sale Classic Semi-Brogue

    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

    Classic Quarter-Brogue - Black

    (1781)

    £39.95

    Comparable High Street Price: £120.50

    Sale Classic City Shoe - Black

    Classic City Shoe - Black

    (2950)

    £39.95 £25.00 Save £14.95

    Comparable High Street Price: £139.50

    Any 2 Pairs for £75

    Classic Cheltenham Brogue

    Classic Cheltenham Brogue

    (177)

    £39.95

    Comparable High Street Price: £120.50

    Any 2 Pairs for £75

    Classic Penny Loafer

    Classic Penny Loafer

    (2120)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £112.00

    Any 2 Pairs for £75

    Classic Cheltenham Brogue In Suede - Mid Brown

    Classic Cheltenham Brogue In Suede - Mid Brown

    (64)

    £39.95

    Comparable High Street Price: £120.50

    Any 2 Pairs for £75

    Classic Sandhurst Shoe

    Classic Sandhurst Shoe

    (1331)

    £39.95

    Comparable High Street Price: £120.50

    Any 2 Pairs for £75

    Classic Monk Shoe

    Classic Monk Shoe

    (1662)

    £39.95

    Comparable High Street Price: £154.99

    Any 2 Pairs for £75

    Classic Penny Loafer

    Classic Penny Loafer

    (75)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £112.00

    Sale Classic Oxford Shoe

    Classic Oxford Shoe

    (195)

    £39.95 £27.50 Save £12.45

    Comparable High Street Price: £133.49

    Any 2 Pairs for £75

    Classic Oxford Shoe

    Classic Oxford Shoe

    (398)

    £39.95

    Comparable High Street Price: £133.49

    Any 2 Pairs for £75

    Classic Suede Oxford Shoe

    Classic Suede Oxford Shoe

    (76)

    £39.95

    Comparable High Street Price: £133.49

    Any 2 Pairs for £75

    Classic Slip-On Deck Shoe

    Classic Slip-On Deck Shoe

    (425)

    £39.95

    Comparable High Street Price: £73.99

    Sale Classic Sandhurst Shoe - Black

    Classic Sandhurst Shoe - Black

    (370)

    £39.95 £27.50 Save £12.45

    Comparable High Street Price: £120.50

    Any 2 Pairs for £75

    Classic Derby Shoe - Black

    Classic Derby Shoe - Black

    (39)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £139.50

    Any 2 Pairs for £75

    Classic Lightweight Brogue - Navy

    Classic Lightweight Brogue - Navy

    (41)

    £39.95

    Comparable High Street Price: £82.24

    Sale Classic Leather Driving Shoe

    Classic Leather Driving Shoe

    (84)

    £39.95 £25.00 Save £14.95

    Comparable High Street Price: £66.55

    Sale Classic Moccasin - Brown

    Classic Moccasin - Brown

    (40)

    £39.95 £25.00 Save £14.95

    Comparable High Street Price: £66.55

    Any 2 Pairs for £75

    Classic Deck Shoe - Blue

    Classic Deck Shoe - Blue

    (41)

    £39.95

    Comparable High Street Price: £73.99

    Any 2 Pairs for £75

    Classic Chichester Shoe - Oxblood

    Classic Chichester Shoe - Oxblood

    (142)

    £39.95

    Comparable High Street Price: £133.49

    Any 2 Pairs for £75

    Classic Moccasin

    Classic Moccasin

    (119)

    £39.95

    Comparable High Street Price: £66.55

    Any 2 Pairs for £75

    Classic Deck Shoe - Tobacco

    Classic Deck Shoe - Tobacco

    (45)

    £39.95

    Comparable High Street Price: £73.99

    Sale Classic Lightweight Brogue - Sand

    Classic Lightweight Brogue - Sand

    (39)

    £39.95 £29.00 Save £10.95

    Comparable High Street Price: £82.24

    Any 2 Pairs for £75

    Classic Driving Shoe

    Classic Driving Shoe

    (109)

    £39.95

    Comparable High Street Price: £66.55

    Any 2 Pairs for £75

    Classic Derby Shoe - Suede

    Classic Derby Shoe - Suede

    (6)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £139.50

    Any 2 Pairs for £75

    Classic Slip-On Deck Shoe - Navy/Brown

    Classic Slip-On Deck Shoe - Navy/Brown

    (425)

    £39.95

    Comparable High Street Price: £73.99

    Any 2 Pairs for £75

    Classic Derby Shoe - Black Suede

    Classic Derby Shoe - Black Suede

    (11)

    £42.50 £39.95 Save £2.55

    Comparable High Street Price: £139.50

    Any 2 Pairs for £75

    Classic Slip-On Deck Shoe - Camel

    Classic Slip-On Deck Shoe - Camel

    (425)

    £39.95

    Comparable High Street Price: £73.99

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