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Over 210,000

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Classic Semi-Brogue - Black

SALE

Classic Semi-Brogue - Black

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

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(3691 reviews)
Classic Oxford Shoe - Black

SALE

Classic Oxford Shoe - Black

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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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(7150 reviews)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

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(1496 reviews)
Classic Quarter-Brogue - Black

SALE

Classic Quarter-Brogue - Black

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

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(1572 reviews)
Classic Monk Shoe - Black

SALE

Classic Monk Shoe - Black

£39.50

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £75

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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(2057 reviews)
Classic Monk Shoe

SALE

Classic Monk Shoe

£39.50

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £75

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

More Info
(1394 reviews)
Prestige Tasselled Loafer - Black

SALE

Prestige Tasselled Loafer - Black

£52.50

Typical High Street Price: £102.67

ANY 2 PAIRS FOR £90

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

More Info
(516 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£39.50

Typical High Street Price: £102.67

ANY 2 PAIRS FOR £75

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

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(309 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£39.50

Typical High Street Price: £89.75

ANY 2 PAIRS FOR £75

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

More Info
(568 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

More Info
(283 reviews)
Prestige Slip-On Deck Shoe

SALE

Prestige Slip-On Deck Shoe

£52.50

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £90

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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(256 reviews)
Classic Slip-On Deck Shoe

SALE

Classic Slip-On Deck Shoe

£39.50

Typical High Street Price: £89.75

ANY 2 PAIRS FOR £75

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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(324 reviews)
Prestige Slip-On Deck Shoe

SALE

Prestige Slip-On Deck Shoe

£52.50

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £90

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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(282 reviews)
Classic Lace-Up Deck Shoe

SALE

Classic Lace-Up Deck Shoe

£26.00

Typical High Street Price: £89.75

Save £63.75

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

SALE

Prestige Cumbria Boot

£52.50

Typical High Street Price: £79.75

ANY 2 PAIRS FOR £90

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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(130 reviews)
Prestige Leather Lace-Up Deck Shoe

SALE

Prestige Leather Lace-Up Deck Shoe

£52.50

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £90

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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(321 reviews)
Prestige Lace-Up Deck Shoe

SALE

Prestige Lace-Up Deck Shoe

£52.50

Typical High Street Price: £116.00

Save £63.50

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
(186 reviews)
Prestige Deck Shoe

SALE

Prestige Deck Shoe

£52.50

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £90

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

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(156 reviews)
Prestige Dress Shoe - Black

SALE

Prestige Dress Shoe - Black

£52.50

Typical High Street Price: £88.30

ANY 2 PAIRS FOR £90

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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(177 reviews)
Prestige Oxford Shoe

SALE

Prestige Oxford Shoe

£30.00

Typical High Street Price: £120.75

Save £90.75

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

SALE

Prestige Chelsea Boot

£52.50

Typical High Street Price: £133.75

ANY 2 PAIRS FOR £90

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

More Info
(238 reviews)
Classic Durham Shoe - Black

SALE

Classic Durham Shoe - Black

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

More Info
(91 reviews)
Prestige Oxford Dress Shoe - Black

SALE

Prestige Oxford Dress Shoe - Black

£52.50

Typical High Street Price: £88.30

ANY 2 PAIRS FOR £90

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

More Info
(56 reviews)
Prestige Chelsea Brogue Boot - Rubber Sole

SALE

Prestige Chelsea Brogue Boot - Rubber Sole

£52.50

Typical High Street Price: £133.75

ANY 2 PAIRS FOR £90

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

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(61 reviews)
Classic Oxford Shoe - Oxblood

SALE

Classic Oxford Shoe - Oxblood

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

More Info
(58 reviews)
Classic Monk Shoe

SALE

Classic Monk Shoe

£39.50

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £75

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

More Info
(14 reviews)
Classic Cheltenham Brogue

SALE

Classic Cheltenham Brogue

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

More Info
(49 reviews)
Classic Suede Oxford Shoe

SALE

Classic Suede Oxford Shoe

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

More Info
(17 reviews)
Prestige Whitworth Brogue

SALE

Prestige Whitworth Brogue

£52.50

Typical High Street Price: £136.33

ANY 2 PAIRS FOR £90

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

More Info
(38 reviews)
Prestige Whitworth Brogue - Navy

SALE

Prestige Whitworth Brogue - Navy

£52.50

Typical High Street Price: £136.33

ANY 2 PAIRS FOR £90

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

More Info
(14 reviews)
Prestige Whitworth Brogue - Black

SALE

Prestige Whitworth Brogue - Black

£52.50

Typical High Street Price: £136.33

ANY 2 PAIRS FOR £90

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

More Info
(16 reviews)
Prestige Country Boot

SALE

Prestige Country Boot

£56.95

Typical High Street Price: £133.75

ANY 2 PAIRS £99

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

More Info
(4 reviews)
Prestige Suede Country Boot

SALE

Prestige Suede Country Boot

£56.95

Typical High Street Price: £133.75

ANY 2 PAIRS £99

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

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

SALE

Prestige Twin Monk Shoe - Oxblood

£52.50

Typical High Street Price: £119.33

ANY 2 PAIRS FOR £90

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

More Info
(19 reviews)
Prestige Oxford Shoe - Rubber Sole

SALE

Prestige Oxford Shoe - Rubber Sole

£54.95

Typical High Street Price: £128.00

ANY 2 PAIRS £99

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

More Info
(6 reviews)
Prestige Split Brogue

SALE

Prestige Split Brogue

£52.50

Typical High Street Price: £136.33

ANY 2 PAIRS FOR £90

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.

More Info
(20 reviews)
Prestige Bartlett Brogue

SALE

Prestige Bartlett Brogue

£54.95

Typical High Street Price: £128.00

ANY 2 PAIRS £99

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

More Info
(19 reviews)
Prestige Suede Bartlett Brogue

SALE

Prestige Suede Bartlett Brogue

£54.95

Typical High Street Price: £128.00

ANY 2 PAIRS £99

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

More Info
(6 reviews)
Prestige Oxford Boot

SALE

Prestige Oxford Boot

£56.95

Typical High Street Price: £133.75

ANY 2 PAIRS £99

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

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

SALE

Classic Penny Loafer Shoe - Black

£39.50

Typical High Street Price: £102.67

ANY 2 PAIRS FOR £75

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

More Info
(3629 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£39.50

Typical High Street Price: £102.67

ANY 2 PAIRS FOR £75

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

More Info
(1878 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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
(2172 reviews)
Classic City Shoe - Black

SALE

Classic City Shoe - Black

£39.50

Typical High Street Price: £128.00

ANY 2 PAIRS FOR £75

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

More Info
(2650 reviews)
Prestige Oxford Shoe - Rubber Sole - Black

SALE

Prestige Oxford Shoe - Rubber Sole - Black

£54.95

Typical High Street Price: £128.00

ANY 2 PAIRS £99

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

More Info
(2006 reviews)
Classic Kempton Shoe - Black

SALE

Classic Kempton Shoe - Black

£39.50

Typical High Street Price: £102.67

ANY 2 PAIRS FOR £75

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

More Info
(1788 reviews)
Classic Kempton Shoe

SALE

Classic Kempton Shoe

£39.50

Typical High Street Price: £102.67

ANY 2 PAIRS FOR £75

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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(2226 reviews)
Prestige Oxford Shoe - Black

SALE

Prestige Oxford Shoe - Black

£52.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £90

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

More Info
(696 reviews)
Prestige Chelsea Boot - Black

SALE

Prestige Chelsea Boot - Black

£52.50

Typical High Street Price: £133.75

ANY 2 PAIRS FOR £90

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

More Info
(1200 reviews)
Prestige Semi-Brogue

SALE

Prestige Semi-Brogue

£52.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £90

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

More Info
(534 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£39.50

Typical High Street Price: £102.67

ANY 2 PAIRS FOR £75

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

More Info
(859 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.