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  1. Classic Oxford Shoe
    £47.95

  2. Flat Front Chino
    £15.00

  3. Classic Cheltenham Brogue
    £47.95

  4. Classic Penny Loafer Shoe
    £47.95

  5. Pleated Chino Trousers
    £15.00

  6. Classic Oxford Shoe
    £47.95

  7. Flat Front Chino
    £15.00

  8. Flat Front Chino
    £15.00

  9. Moleskin Jeans
    £20.00

  10. Long Sleeve Weekend Shirt
    £22.50

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

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

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94% (165)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £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% (838)
Classic Semi-Brogue

Classic Semi-Brogue

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

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

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92% (118)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

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

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £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% (244)
Classic Monk Shoe

Classic Monk Shoe

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

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

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90% (153)
Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

£54.95

Typical High Street Price: £132.67

Save £77.72

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

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92% (63)
Classic Durham Shoe

Classic Durham Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £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: £132.67

ANY TWO FOR £80

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

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86% (77)
Classic Deck Shoe

Classic Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY TWO FOR £80

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

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90% (138)
Prestige Derby Shoe

Prestige Derby Shoe

£49.95

Typical High Street Price: £91.32

Save £41.37

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

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94% (3)
Classic Oxford Shoe

Classic Oxford Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

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

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94% (112)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£49.95

Typical High Street Price: £111.00

Save £61.05

Prestige Leather Slip-On Boat Shoe - made with the finest Italian leather uppers or a luxury finish and unbeatable comfort and durability.

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90% (101)
Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY TWO FOR £80

These Classic Slip-On Boat Shoes are handmade by Samuel Windsor. These designer slip-on shoes are crafted using only the finest leathers.

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86% (135)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£49.95

Typical High Street Price: £111.00

Save £61.05

Our Prestige Slip-on Boat Shoes with contrasting colours is the epitome of casual sophistication. Visit us now for great offers on leather deck shoes.

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90% (122)
Classic Lace-Up Deck Shoe

Classic Lace-Up Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY TWO FOR £80

Our Classic Lace-Up Boat Shoes are handmade by Samuel Windsor. These designer lace-up shoes are crafted using only the finest leathers.

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88% (49)
Prestige Cumbria Boot

Prestige Cumbria Boot

£54.95

Typical High Street Price: £81.00

Save £26.05

Prestige Cumbria Boot - Mid Brown, a lace-up shoe with an exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

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92% (56)
Prestige Lace-Up Deck Shoe

Prestige Lace-Up Deck Shoe

£49.95

Typical High Street Price: £111.00

Save £61.05

Prestige Leather Lace-Up Boat Shoe - exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

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90% (121)
Prestige Lace-Up Deck Shoe

Prestige Lace-Up Deck Shoe

£49.95

Typical High Street Price: £111.00

Save £61.05

Our Prestige Lace-Up Boat Shoes with contrasting colours is the epitome of casual sophistication. Visit us now for great offers on leather deck shoes.

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94% (55)
Prestige Lightweight Brogue

Prestige Lightweight Brogue

£49.95

Typical High Street Price: £91.32

Save £41.37

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 Deck Shoe

Prestige Deck Shoe

£49.95

Typical High Street Price: £111.00

Save £61.05

These Prestige deck shoes are supremely comfortable, fabulously affordable and crafted using Italian leather. Visit now for great offers.

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90% (77)
Prestige Dress Shoe

Prestige Dress Shoe

£54.95

Typical High Street Price: £102.50

Save £47.55

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% (74)
Classic Semi-Brogue

Classic Semi-Brogue

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

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

More Info
88% (69)
Classic Quarter-Brogue

Classic Quarter-Brogue

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

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

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92% (39)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

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

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92% (47)
Prestige Oxford Shoe

Prestige Oxford Shoe

£54.95

Typical High Street Price: £130.75

Save £75.80

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

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86% (26)
Prestige Chelsea Boot

Prestige Chelsea Boot

£54.95

Typical High Street Price: £152.00

Save £97.05

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

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94% (86)
Prestige Tasselled Loafer

Prestige Tasselled Loafer

£54.95

Typical High Street Price: £132.67

Save £77.72

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

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76% (25)
Classic Durham Shoe

Classic Durham Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £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

£54.95

Typical High Street Price: £102.50

Save £47.55

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% (20)
Prestige Chelsea Brogue Boot - Rubber Sole

Prestige Chelsea Brogue Boot - Rubber Sole

£59.95

Typical High Street Price: £152.00

Save £92.05

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

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86% (42)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £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% (413)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

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

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90% (189)
Classic Oxford Shoe

Classic Oxford Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £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% (294)
Classic City Shoe - Black

Classic City Shoe - Black

£47.95

Typical High Street Price: £128.00

ANY TWO FOR £80

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

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86% (104)
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% (119)
Classic Richmond Shoe - Black

Classic Richmond Shoe - Black

£47.95

Typical High Street Price: £128.00

ANY TWO FOR £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% (73)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

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

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92% (173)
Classic Kempton Shoe

Classic Kempton Shoe

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £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% (333)
Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

£54.95

Typical High Street Price: £130.75

Save £75.80

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

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90% (72)
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.

More Info
94% (157)
Prestige Semi-Brogue

Prestige Semi-Brogue

£54.95

Typical High Street Price: £130.75

Save £75.80

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

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92% (35)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

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

More Info
90% (102)

We hope you've found the perfect gentlemen's leather shoe for you. We pride ourselves on having an extensive selection of colours, sizes and styles, from luxury formal shoes to comfortable casual shoes. For the ultimate in comfortable footwear, be sure to browse our quality collection of men's leather slippers. If you can't find what you're looking for please contact us.