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Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£49.95

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £85

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

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(3707 reviews)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£49.95

Typical High Street Price: £133.25

ANY 2 PAIRS FOR £85

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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(7205 reviews)
Classic Semi-Brogue

Classic Semi-Brogue

£49.95

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £85

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

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(1503 reviews)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£49.95

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £85

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

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(1581 reviews)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£49.95

Typical High Street Price: £136.00

ANY 2 PAIRS FOR £85

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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(2072 reviews)
Classic Monk Shoe

Classic Monk Shoe

£49.95

Typical High Street Price: £136.00

ANY 2 PAIRS FOR £85

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

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(1403 reviews)
Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

£55.00

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £99

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

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(522 reviews)
Classic Penny Loafer

Classic Penny Loafer

£49.95

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £85

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

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(311 reviews)
Classic Deck Shoe

Classic Deck Shoe

£49.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £85

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

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(578 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£49.95

Typical High Street Price: £133.25

ANY 2 PAIRS FOR £85

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

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(291 reviews)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£55.00

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £99

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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(260 reviews)
Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£49.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £85

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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(331 reviews)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£55.00

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £99

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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(285 reviews)
Classic Lace-Up Deck Shoe

Classic Lace-Up Deck Shoe

£34.95

Typical High Street Price: £92.25

Save £57.30

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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(142 reviews)
Prestige Cumbria Boot

Prestige Cumbria Boot

£59.50

Typical High Street Price: £81.50

ANY 2 FOR £110

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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(133 reviews)
Prestige Leather Lace-Up Deck Shoe

Prestige Leather Lace-Up Deck Shoe

£55.00

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £99

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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(322 reviews)
Prestige Lace-Up Deck Shoe

Prestige Lace-Up Deck Shoe

£55.00

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £99

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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(187 reviews)
Prestige Deck Shoe

Prestige Deck Shoe

£55.00

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £99

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

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(162 reviews)
Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

£55.00

Typical High Street Price: £88.30

ANY 2 PAIRS FOR £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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(184 reviews)
Prestige Oxford Shoe

Prestige Oxford Shoe

£39.95

Typical High Street Price: £133.25

Save £93.30

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

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(83 reviews)
Prestige Chelsea Boot

Prestige Chelsea Boot

£59.50

Typical High Street Price: £183.00

ANY 2 FOR £110

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

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(245 reviews)
Classic Durham Shoe - Black

Classic Durham Shoe - Black

£39.95

Typical High Street Price: £128.50

Save £88.55

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

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(93 reviews)
Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

£55.00

Typical High Street Price: £88.30

ANY 2 PAIRS FOR £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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(62 reviews)
Prestige Chelsea Brogue Boot - Rubber Sole

Prestige Chelsea Brogue Boot - Rubber Sole

£44.95

Typical High Street Price: £183.00

Save £138.05

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

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(61 reviews)
Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

£49.95

Typical High Street Price: £133.25

ANY 2 PAIRS FOR £85

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

More Info
(85 reviews)
Classic Monk Shoe

Classic Monk Shoe

£49.95

Typical High Street Price: £136.00

ANY 2 PAIRS FOR £85

These handmade Monk Shoes are another traditional classic from Samuel Windsor, painstakingly constructed from over 50 natural components.

More Info
(16 reviews)
Classic Penny Loafer

Classic Penny Loafer

£49.95

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £85

More Info
(22 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£49.95

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £85

Buy classic black brogues from Samuel Windsor. Our handmade brogues offer Goodyear welted construction for long lasting quality. Visit now for great offers.

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(69 reviews)
Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

£49.95

Typical High Street Price: £133.25

ANY 2 PAIRS FOR £85

Classic Suede Oxford Shoes in black from Samuel Windsor. Visit now for outstanding quality and fantastic offers.

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(29 reviews)
Prestige Whitworth Brogue

Prestige Whitworth Brogue

£59.50

Typical High Street Price: £138.00

ANY 2 FOR £110

For a truly contemporary take on the tradition and heritage of the brogue, look no further than our Whitworth styles.

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(46 reviews)
Prestige Whitworth Brogue - Navy

Prestige Whitworth Brogue - Navy

£45.00

Typical High Street Price: £138.00

Save £93.00

Prestige Whitworth Brogue in Navy from Samuel Windsor. Visit now for quality brogues at outstanding prices.

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(20 reviews)
Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

£59.50

Typical High Street Price: £138.00

ANY 2 FOR £110

Prestige Whitworth Brogue in Black from Samuel Windsor. Visit now for quality brogues at outstanding prices.

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(20 reviews)
Prestige Country Boot

Prestige Country Boot

£39.95

Typical High Street Price: £183.00

Save £143.05

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

More Info
(6 reviews)
Prestige Suede Country Boot

Prestige Suede Country Boot

£39.95

Typical High Street Price: £183.00

Save £143.05

Prestige Suede Country Boot - Brown, available online from Samuel Windsor. Premium quality at outstanding prices. Visit now for great offers.

More Info
(21 reviews)
Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

£55.00

Typical High Street Price: £136.00

ANY 2 PAIRS FOR £99

Suave and sophisticated; the wonderfully hand crafted Prestige Oxblood Twin Monk.

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(23 reviews)
Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

£65.00

Typical High Street Price: £128.00

ANY 2 FOR £110

Classic Oxford shoe with rubber sole. Goodyear Welted men’s shoes made from Italian leather. Visit now for great offers.

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(9 reviews)
Prestige Split Brogue

Prestige Split Brogue

£59.50

Typical High Street Price: £138.00

ANY 2 FOR £110

For a truly contemporary take on the tradition and heritage of the brogue, look no further. These split brogues, offer two contrasting shades, making them just as perfect for formal events, as they are for more casual wear.

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(22 reviews)
Prestige Bartlett Brogue

Prestige Bartlett Brogue

£65.00

Typical High Street Price: £128.00

ANY 2 FOR £110

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

More Info
(29 reviews)
Prestige Bartlett Brogue

Prestige Bartlett Brogue

£65.00

Typical High Street Price: £128.00

ANY 2 FOR £110

Prestige Bartlett Brogue available online from Samuel Windsor. Premium quality at outstanding prices. Visit now for great offers.

More Info
(8 reviews)
Prestige Oxford Boot

Prestige Oxford Boot

£60.00

Typical High Street Price: £183.00

Save £123.00

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

More Info
(31 reviews)
Classic Deck Shoe - Tobacco

NEW

Classic Deck Shoe - Tobacco

£49.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £85

Classic Deck Shoe from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

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Classic Deck Shoe - Blue

NEW

Classic Deck Shoe - Blue

£49.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £85

Classic Deck Shoe from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

More Info
(3 reviews)
Classic Deck Shoe - Navy/Brown

NEW

Classic Deck Shoe - Navy/Brown

£49.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £85

Classic Deck Shoe from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

More Info
(5 reviews)
Prestige Lightweight Oxford - Brown

NEW

Prestige Lightweight Oxford - Brown

£55.00

Typical High Street Price: £85.00

ANY 2 PAIRS FOR £99

These Lightweight Prestige Collection summer shoes feature an exceptionally light and comfortable sole

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Prestige Lightweight Derby - Tan

NEW

Prestige Lightweight Derby - Tan

£55.00

Typical High Street Price: £85.00

ANY 2 PAIRS FOR £99

These Lightweight Prestige Collection summer shoes feature an exceptionally light and comfortable sole

More Info
(3 reviews)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£49.95

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £85

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

More Info
(3649 reviews)
Classic Penny Loafer

Classic Penny Loafer

£49.95

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £85

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

More Info
(1887 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£49.95

Typical High Street Price: £133.25

ANY 2 PAIRS FOR £85

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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(2180 reviews)
Classic City Shoe - Black

Classic City Shoe - Black

£49.95

Typical High Street Price: £128.00

ANY 2 PAIRS FOR £85

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

More Info
(2655 reviews)
Prestige Oxford Shoe - Rubber Sole - Black

Prestige Oxford Shoe - Rubber Sole - Black

£65.00

Typical High Street Price: £128.00

ANY 2 FOR £110

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

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(2013 reviews)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£49.95

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £85

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

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(1797 reviews)
Classic Kempton Shoe

Classic Kempton Shoe

£49.95

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £85

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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(2234 reviews)
Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

£55.00

Typical High Street Price: £133.25

ANY 2 PAIRS FOR £99

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

More Info
(702 reviews)
Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

£59.50

Typical High Street Price: £183.00

ANY 2 FOR £110

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

More Info
(1214 reviews)
Prestige Semi-Brogue

Prestige Semi-Brogue

£55.00

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £99

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

More Info
(536 reviews)
Classic Penny Loafer

Classic Penny Loafer

£49.95

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £85

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

More Info
(864 reviews)

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.