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  1. Classic Oxford Shoe
    £47.95

  2. Classic Cheltenham Brogue
    £47.95

  3. Pleated Chino Trousers
    £17.50

  4. Classic Penny Loafer Shoe
    £47.95

  5. Classic Oxford Shoe
    £47.95

  6. Moleskin Jeans
    £20.00

  7. Flat Front Chino
    £17.50

  8. Classic Tweed Jacket
    £69.00

  9. Prestige Oxford Shoe
    £64.95

  10. Classic Monk Shoe
    £47.95

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Semi-Brogues - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (164)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

The Samuel Windsor commitment to quality ensures these handmade Classic black Oxford shoes will prove to be the finest, most comfortable and hardest wearing men's leather shoes you will ever invest in.

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92% (855)
Classic Semi-Brogue

Classic Semi-Brogue

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Suede Semi-Brogues - Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (119)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Plain Toe Cap Quarter Brogue - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (128)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

These handmade Monk Shoes is another traditional classic from Samuel Windsor, painstakingly constructed from over 50 natural components. The monk strap leather design is powerful in appearance.

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94% (248)
Classic Monk Shoe

Classic Monk Shoe

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

Classic Monk Shoes - Chestnut Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (158)
Prestige Brogue - Rubber Sole

Prestige Brogue - Rubber Sole

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

Prestige Brogue: Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (88)
Prestige Kensington Boot - Rubber Sole

Prestige Kensington Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Kensington Boot - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (57)
Classic Durham Shoe

Classic Durham Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Durham Shoe - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (60)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

Classic Penny Loafer - Dark Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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84% (79)
Prestige Kensington Boot - Rubber Sole - Black

Prestige Kensington Boot - Rubber Sole - Black

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Kensington Boot - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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86% (53)
Prestige Derby Shoe

Prestige Derby Shoe

£64.95

Typical High Street Price: £126.33

ANY 2 PAIRS £99

Prestige Derby Shoe - Navy Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (2)
Classic Oxford Shoe

Classic Oxford Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Oxford Shoes - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (111)
Prestige Lightweight Brogue

Prestige Lightweight Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Lightweight Brogue - Tobacco, a brogue shoe with an exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

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Prestige Leather/Canvas Brogue

SALE

Prestige Leather/Canvas Brogue

£27.50

Typical High Street Price: £129.50

Save £102.00

Leather and canvas brogues from our Prestige range are the pinnacle of versatility. Choose from a range of colours at Samuel Windsor online.

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90% (46)
Prestige Leather/Canvas Brogue

SALE

Prestige Leather/Canvas Brogue

£25.00

Typical High Street Price: £129.50

Save £104.50

Prestige Leather/Canvas Brogue from our Prestige range are the pinnacle of versatility.

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94% (78)
Prestige Dress Shoe

Prestige Dress Shoe

£64.95

Typical High Street Price: £92.25

ANY 2 PAIRS £99

Shopping for men's dress shoes? Add the finishing touch to your formal outfit with Samuel Windsor prestige dress shoes, made from fine Italian leather.

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96% (77)
Prestige Country Boot - Rubber Sole

Prestige Country Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Country Boot - Antique Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (56)
Prestige Country Boot - Rubber Sole

Prestige Country Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Country Boot, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (58)
Classic Oxford Shoe - Cigar

Classic Oxford Shoe - Cigar

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Oxford Shoes - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (61)
Classic Semi-Brogue

Classic Semi-Brogue

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Semi-Brogues - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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86% (68)
Classic Quarter-Brogue

Classic Quarter-Brogue

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Quarter-Brogues - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (41)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Sandhurst Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (48)
Prestige Oxford Shoe

Prestige Oxford Shoe

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Featuring a classic Oxford shoe design, these Goodyear Welted men’s shoes offer all the luxury you could ask for.

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84% (27)
Prestige Chelsea Boot

Prestige Chelsea Boot

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boot, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (88)
Prestige Semi Brogue

Prestige Semi Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Brogue, online from Samuel Windsor. Tailored quality at outstanding prices.

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96% (35)
Prestige Oxford

Prestige Oxford

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Oxford Shoe, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (71)
Prestige Split Brogue

Prestige Split Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Make an entrance with Samuel Windsor Prestige Split Brogues. Its two-tone style and punch detailing make for an outstanding finish.

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90% (69)
Prestige Twin Monk

Prestige Twin Monk

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Twin Monk, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (60)
Prestige Brogue

Prestige Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Black Brogues, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (78)
Classic Durham Shoe

Classic Durham Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Classic Durham Shoe, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (45)
Prestige Oxford Dress Shoe

Prestige Oxford Dress Shoe

£64.95

Typical High Street Price: £92.25

ANY 2 PAIRS £99

Shopping for mens dress shoes? Add the finishing touch to your formal outfit with prestige Oxford dress shoes, from Samuel Windsor online.

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90% (18)
Prestige Chelsea Brogue Boot - Rubber Sole

Prestige Chelsea Brogue Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Brogue Boot - Rubber Sole is made by hand using Goodyear Welted construction.

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84% (40)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Buy Prestige Chukka Boots from Samuel Windsor. Rubber soles and Italian leather suede make this classic boot the perfect choice for a smart casual outfit.

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94% (22)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Buy Burgundy Chukka Boots from Samuel Windsor. Rubber soles and Italian leather suede make this classic boot the perfect choice for a smart casual outfit.

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90% (12)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

These black Penny Loafer men's leather shoes from Samuel Windsor are classic formal shoes combined with supple, easy slip-on access.

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90% (420)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

Classic Penny Loafer Shoe - Chestnut Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (196)
Classic Oxford Shoe

Classic Oxford Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Crafted using time honoured shoe making techniques, these Samuel Windsor Classic Oxford Shoes in chestnut brown are classic formal shoes or office shoes.

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94% (289)
Classic City Shoe - Black

Classic City Shoe - Black

£47.95

Typical High Street Price: £126.33

ANY 2 PAIRS £80

Classic City Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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86% (105)
Prestige Oxford Shoe - Rubber Sole - Black

Prestige Oxford Shoe - Rubber Sole - Black

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

Black Oxford Shoes Rubber Sole, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (117)
Classic Richmond Shoe - Black

Classic Richmond Shoe - Black

£47.95

Typical High Street Price: £126.33

ANY 2 PAIRS £80

Great office shoes, these Samuel Windsor Richmond Classics mens black shoes are handmade, incorporating a leather lining which is both breathable and seamless.

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88% (70)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

Classic Kempton Black Shoe - Slip-On, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (175)
Classic Kempton Shoe

Classic Kempton Shoe

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

Designed to look good with formal or casual wear, these Samuel Windsor real leather Kempton men's leather shoes, men's brown shoes, are an essential addition to any gentleman's wardrobe.

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94% (337)
Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Oxford Black Shoe - Italian Leather Upper, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (77)
Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boots: Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (163)
Prestige Suede Chelsea Boot

Prestige Suede Chelsea Boot

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boots: Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (81)
Prestige Semi-Brogue

Prestige Semi-Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Semi-Brogue - Tan - Italian Leather Upper, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (36)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

Classic Penny Loafer Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (102)