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End of season sale Save up to 70% on typical high street prices

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Samuel Windsor end of season sale

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93%
111,895

Independent customer reviews

Most Popular

  1. Classic Oxford Shoe
    £35.00

  2. Classic Cheltenham Brogue
    £35.00

  3. Classic Penny Loafer Shoe
    £35.00

  4. Tattersall Shirt
    £15.00

  5. Tattersall Shirt
    £15.00

  6. Tattersall Shirt
    £15.00

  7. Classic Oxford Shoe
    £35.00

  8. Classic Monk Shoe
    £35.00

  9. Classic Semi-Brogue
    £35.00

  10. Outdoor Mule
    £29.95

Classic Semi-Brogue - Black

SALE

Classic Semi-Brogue - Black

£35.00

Typical High Street Price: £129.50

Save £94.50

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

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94% (168)
Classic Oxford Shoe - Black

SALE

Classic Oxford Shoe - Black

£35.00

Typical High Street Price: £129.50

Save £94.50

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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94% (866)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£35.00

Typical High Street Price: £129.50

Save £94.50

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

SALE

Classic Quarter-Brogue - Black

£35.00

Typical High Street Price: £129.50

Save £94.50

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

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94% (133)
Classic Monk Shoe - Black

SALE

Classic Monk Shoe - Black

£35.00

Typical High Street Price: £131.00

Save £96.00

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% (247)
Classic Monk Shoe

SALE

Classic Monk Shoe

£35.00

Typical High Street Price: £131.00

Save £96.00

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

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92% (164)
Prestige Tasselled Loafer - Black

SALE

Prestige Tasselled Loafer - Black

£45.00

Typical High Street Price: £131.00

Save £86.00

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

More Info
92% (69)
Classic Durham Shoe

SALE

Classic Durham Shoe

£35.00

Typical High Street Price: £129.50

Save £94.50

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

More Info
88% (59)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £131.00

Save £96.00

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

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86% (84)
Classic Deck Shoe

SALE

Classic Deck Shoe

£35.00

Typical High Street Price: £88.50

Save £53.50

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

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90% (148)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£35.00

Typical High Street Price: £129.50

Save £94.50

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

More Info
94% (110)
Prestige Slip-On Deck Shoe

SALE

Prestige Slip-On Deck Shoe

£45.00

Typical High Street Price: £111.00

Save £66.00

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% (131)
Classic Slip-On Deck Shoe

SALE

Classic Slip-On Deck Shoe

£35.00

Typical High Street Price: £88.50

Save £53.50

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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88% (157)
Prestige Slip-On Deck Shoe

SALE

Prestige Slip-On Deck Shoe

£45.00

Typical High Street Price: £111.00

Save £66.00

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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88% (137)
Classic Lace-Up Deck Shoe

SALE

Classic Lace-Up Deck Shoe

£35.00

Typical High Street Price: £88.50

Save £53.50

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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90% (56)
Prestige Cumbria Boot

SALE

Prestige Cumbria Boot

£47.50

Typical High Street Price: £81.00

Save £33.50

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

SALE

Prestige Lace-Up Deck Shoe

£45.00

Typical High Street Price: £111.00

Save £66.00

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% (145)
Prestige Lace-Up Deck Shoe

SALE

Prestige Lace-Up Deck Shoe

£45.00

Typical High Street Price: £111.00

Save £66.00

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.

More Info
96% (62)
Prestige Deck Shoe

SALE

Prestige Deck Shoe

£45.00

Typical High Street Price: £111.00

Save £66.00

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

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90% (74)
Prestige Dress Shoe

SALE

Prestige Dress Shoe

£45.00

Typical High Street Price: £92.25

Save £47.25

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% (81)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£35.00

Typical High Street Price: £129.50

Save £94.50

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

More Info
88% (73)
Classic Quarter-Brogue

SALE

Classic Quarter-Brogue

£35.00

Typical High Street Price: £129.50

Save £94.50

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

More Info
94% (42)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£35.00

Typical High Street Price: £129.50

Save £94.50

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

More Info
88% (45)
Prestige Oxford Shoe

SALE

Prestige Oxford Shoe

£45.00

Typical High Street Price: £129.50

Save £84.50

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% (28)
Prestige Deck Boot

SALE

Prestige Deck Boot

£25.00

Typical High Street Price: £111.00

Save £86.00

Sturdy design meets the styling of a deck shoe in this Prestige Deck Boot.

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90% (110)
Prestige Chelsea Boot

SALE

Prestige Chelsea Boot

£47.50

Typical High Street Price: £148.25

Save £100.75

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

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94% (85)
Prestige Tasselled Loafer

SALE

Prestige Tasselled Loafer

£45.00

Typical High Street Price: £131.00

Save £86.00

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

More Info
76% (19)
Classic Durham Shoe

SALE

Classic Durham Shoe

£35.00

Typical High Street Price: £129.50

Save £94.50

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

More Info
86% (38)
Prestige Oxford Dress Shoe

SALE

Prestige Oxford Dress Shoe

£45.00

Typical High Street Price: £92.25

Save £47.25

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

More Info
88% (13)
Prestige Chelsea Brogue Boot - Rubber Sole

SALE

Prestige Chelsea Brogue Boot - Rubber Sole

£49.95

Typical High Street Price: £148.25

Save £98.30

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

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86% (33)
Classic Penny Loafer Shoe - Black

SALE

Classic Penny Loafer Shoe - Black

£35.00

Typical High Street Price: £131.00

Save £96.00

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

More Info
90% (434)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £131.00

Save £96.00

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

More Info
90% (209)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£35.00

Typical High Street Price: £129.50

Save £94.50

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

More Info
94% (291)
Classic City Shoe - Black

SALE

Classic City Shoe - Black

£35.00

Typical High Street Price: £126.33

Save £91.33

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

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86% (106)
Prestige Oxford Shoe - Rubber Sole - Black

SALE

Prestige Oxford Shoe - Rubber Sole - Black

£47.50

Typical High Street Price: £106.17

Save £58.67

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

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90% (114)
Classic Richmond Shoe - Black

SALE

Classic Richmond Shoe - Black

£35.00

Typical High Street Price: £126.33

Save £91.33

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

SALE

Classic Kempton Shoe - Black

£35.00

Typical High Street Price: £131.00

Save £96.00

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

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92% (174)
Classic Kempton Shoe

SALE

Classic Kempton Shoe

£35.00

Typical High Street Price: £131.00

Save £96.00

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% (345)
Prestige Oxford Shoe - Black

SALE

Prestige Oxford Shoe - Black

£45.00

Typical High Street Price: £129.50

Save £84.50

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

More Info
90% (73)
Prestige Chelsea Boot - Black

SALE

Prestige Chelsea Boot - Black

£47.50

Typical High Street Price: £148.25

Save £100.75

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

More Info
94% (157)
Prestige Semi-Brogue

SALE

Prestige Semi-Brogue

£45.00

Typical High Street Price: £129.50

Save £84.50

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

More Info
92% (37)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £131.00

Save £96.00

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

More Info
90% (107)

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.