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92%
114,455

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Most Popular

  1. Classic Oxford Shoe
    £37.50

  2. Classic Cheltenham Brogue
    £37.50

  3. Classic Penny Loafer Shoe
    £37.50

  4. Classic Oxford Shoe
    £37.50

  5. Classic Monk Shoe
    £37.50

  6. Classic Semi-Brogue
    £37.50

  7. Classic Penny Loafer
    £37.50

  8. Classic Sandhurst Shoe
    £37.50

  9. Classic Penny Loafer
    £37.50

  10. Classic Kempton Shoe
    £37.50

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£37.50

Typical High Street Price: £130.75

Save £93.25

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

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94% (166)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£37.50

Typical High Street Price: £130.75

Save £93.25

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% (819)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£37.50

Typical High Street Price: £130.75

Save £93.25

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

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92% (126)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£37.50

Typical High Street Price: £132.67

Save £95.17

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% (237)
Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

£49.95

Typical High Street Price: £132.67

Save £82.72

Prestige Tasselled Loafer - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (57)
Churchill Suede Moccasin Slipper

SALE

Churchill Suede Moccasin Slipper

£25.00

Churchill Suede Moccasin: Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (29)
Prestige Brogue - Rubber Sole - Black

Prestige Brogue - Rubber Sole - Black

£54.95

Typical High Street Price: £107.83

Save £52.88

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

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90% (71)
Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

£37.50

Typical High Street Price: £130.75

Save £93.25

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

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88% (57)
Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

£49.95

Typical High Street Price: £132.67

Save £82.72

Prestige Penny Loafer - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (76)
Prestige Monk Shoe - Rubber Sole - Black

Prestige Monk Shoe - Rubber Sole - Black

£64.95

Typical High Street Price: £107.83

Save £42.88

Prestige Monk Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (23)
Prestige Kensington Boot - Rubber Sole - Black

Prestige Kensington Boot - Rubber Sole - Black

£59.95

Typical High Street Price: £152.00

Save £92.05

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

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84% (40)
Prestige Dress Shoe

Prestige Dress Shoe

£49.95

Typical High Street Price: £93.00

Save £43.05

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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94% (71)
Prestige Semi Brogue

Prestige Semi Brogue

£54.95

Typical High Street Price: £130.75

Save £75.80

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

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92% (50)
Prestige Oxford

Prestige Oxford

£54.95

Typical High Street Price: £128.33

Save £73.38

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

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90% (60)
Prestige Twin Monk

Prestige Twin Monk

£49.95

Typical High Street Price: £132.67

Save £82.72

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

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90% (49)
Prestige Brogue

Prestige Brogue

£54.95

Typical High Street Price: £128.33

Save £73.38

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

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90% (49)
Classic Durham Shoe

Classic Durham Shoe

£37.50

Typical High Street Price: £130.75

Save £93.25

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

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88% (48)
Classic Monk Brogue

Classic Monk Brogue

£37.50

Typical High Street Price: £132.67

Save £95.17

These monk brogue shoes have been producted using the finest Italian leathers and using a goodyear welted construction which offers and unbeatable combination of durability and comfort and an exceptional price.

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92% (60)
Prestige Oxford Dress Shoe

Prestige Oxford Dress Shoe

£49.95

Typical High Street Price: £93.00

Save £43.05

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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92% (22)
Prestige Balham Boot - Black

NEW

Prestige Balham Boot - Black

£54.95

Typical High Street Price: £85.75

Save £30.80

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

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Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£37.50

Typical High Street Price: £132.67

Save £95.17

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% (396)
Classic City Shoe - Black

Classic City Shoe - Black

£37.50

Typical High Street Price: £128.00

Save £90.50

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

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86% (103)
Prestige Oxford Shoe - Rubber Sole - Black

Prestige Oxford Shoe - Rubber Sole - Black

£54.95

Typical High Street Price: £107.83

Save £52.88

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

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88% (116)
Classic Richmond Shoe - Black

Classic Richmond Shoe - Black

£37.50

Typical High Street Price: £128.00

Save £90.50

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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90% (75)
Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

£37.50

Typical High Street Price: £130.75

Save £93.25

Buy classic black brogues. A staple shoe for the modern man, our handmade classic cheltenham brogues are the perfect shoe for formal and casual occasions.

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92% (451)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£37.50

Typical High Street Price: £132.67

Save £95.17

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

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92% (166)
Outdoor Mule - Black

Outdoor Mule - Black

£37.50

Typical High Street Price: £48.50

ANY 2 FOR £65

Handmade using the finest nappa leathers these slippers are the perfect accompaniment to a dressing gown and a day lazing around the house.

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92% (155)
Albert Slipper - Black

Albert Slipper - Black

£37.50

Typical High Street Price: £62.50

ANY 2 FOR £65

Handmade Black Churchill Albert Leather Lined Slippers, hand-crafted using the finest nappa leathers. Visit Samuel Windsor now for amazing offers.

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88% (79)
Grecian Slipper - Black

SALE

Grecian Slipper - Black

£25.00

Typical High Street Price: £62.50

Save £37.50

These Black Churchill Grecian Wool Lined Slippers have been hand-crafted using the finest nappa leathers. Visit Samuel Windsor online for great offers.

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90% (46)
Mule - Black

Mule - Black

£37.50

Typical High Street Price: £62.50

ANY 2 FOR £65

Handmade Black Churchill Mule Part Leather Lined Slippers, hand-crafted using the finest nappa leathers. Visit Samuel Windsor online now for amazing offers.

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90% (39)
Prestige Gibson Shoe

Prestige Gibson Shoe

£54.95

Typical High Street Price: £107.83

Save £52.88

These Goodyear Welted, Prestige Gibson shoes, featuring Italian grained leather uppers, as well as a practical rubber sole, they have country styling, and are ideal as a more subtle choice of quality men’s shoe.

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92% (39)
Shearling Mule - Black

SALE

Shearling Mule - Black

£25.00

Typical High Street Price: £61.75

Save £36.75

Shearling Mule - Black - Winter mules, the ultimate slipper. Soft, supple and warm water-resistant leather, at that time of year when you need it most.

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100% (6)
Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

£49.95

Typical High Street Price: £130.75

Save £80.80

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

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90% (73)
Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

£54.95

Typical High Street Price: £152.00

Save £97.05

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

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94% (153)
Prestige Semi-Brogue - Black

Prestige Semi-Brogue - Black

£49.95

Typical High Street Price: £130.75

Save £80.80

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

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86% (34)

Samuel Windsor black shoes are available to order in sizes 5 to 14. Our range features classic styles including sleek black Oxford shoes, bohemian black brogues and sturdy black Chelsea boots. For a less formal look, try our selection of brown shoes, perfect for smart casual wear at weekends.