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Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

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

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(3728 reviews)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£39.50

Typical High Street Price: £134.74

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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(7312 reviews)
Classic Semi-Brogue

Classic Semi-Brogue

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

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

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(1516 reviews)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£39.50

Typical High Street Price: £125.99

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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(1605 reviews)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£39.50

Typical High Street Price: £124.33

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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(2091 reviews)
Classic Monk Shoe

Classic Monk Shoe

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

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(1426 reviews)
Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

£47.50

Typical High Street Price: £124.33

Save £76.83

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

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(532 reviews)
Classic Penny Loafer

Classic Penny Loafer

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

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(325 reviews)
Classic Deck Shoe

Classic Deck Shoe

£39.50

Typical High Street Price: £94.75

ANY 2 PAIRS FOR £75

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

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(607 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

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

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(309 reviews)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£47.50

Typical High Street Price: £119.99

Save £72.49

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

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(297 reviews)
Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£39.50

Typical High Street Price: £94.75

ANY 2 PAIRS FOR £75

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

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(353 reviews)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£47.50

Typical High Street Price: £119.99

Save £72.49

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

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(297 reviews)
Prestige Cumbria Boot

Prestige Cumbria Boot

£49.50

Typical High Street Price: £92.50

Save £43.00

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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(140 reviews)
Prestige Leather Lace-Up Deck Shoe

Prestige Leather Lace-Up Deck Shoe

£47.50

Typical High Street Price: £119.99

Save £72.49

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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(348 reviews)
Prestige Lace-Up Deck Shoe

Prestige Lace-Up Deck Shoe

£47.50

Typical High Street Price: £119.99

Save £72.49

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

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(202 reviews)
Prestige Deck Shoe

Prestige Deck Shoe

£47.50

Typical High Street Price: £119.99

Save £72.49

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

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(186 reviews)
Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

£47.50

Typical High Street Price: £114.75

Save £67.25

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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(192 reviews)
Prestige Chelsea Boot

Prestige Chelsea Boot

£49.50

Typical High Street Price: £183.00

Save £133.50

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

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(259 reviews)
Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

£47.50

Typical High Street Price: £114.75

Save £67.25

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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(71 reviews)
Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

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

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(133 reviews)
Classic Monk Shoe

Classic Monk Shoe

£28.95

Typical High Street Price: £124.33

Save £95.38

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

More Info
(23 reviews)
Classic Penny Loafer

Classic Penny Loafer

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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(28 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£39.50

Typical High Street Price: £125.99

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.

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(114 reviews)
Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

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

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(44 reviews)
Prestige Whitworth Brogue

Prestige Whitworth Brogue

£49.50

Typical High Street Price: £161.65

Save £112.15

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

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(79 reviews)
Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

£49.50

Typical High Street Price: £161.65

Save £112.15

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

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(37 reviews)
Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

£47.50

Typical High Street Price: £124.33

Save £76.83

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

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(35 reviews)
Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

£52.50

Typical High Street Price: £129.98

Save £77.48

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

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(16 reviews)
Prestige Split Brogue

Prestige Split Brogue

£49.50

Typical High Street Price: £161.65

Save £112.15

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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(37 reviews)
Prestige Bartlett Brogue

Prestige Bartlett Brogue

£52.50

Typical High Street Price: £129.98

Save £77.48

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

More Info
(44 reviews)
Prestige Bartlett Brogue

Prestige Bartlett Brogue

£37.95

Typical High Street Price: £129.98

Save £92.03

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

More Info
(11 reviews)
Classic Deck Shoe - Tobacco

Classic Deck Shoe - Tobacco

£26.50

Typical High Street Price: £94.75

Save £68.25

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

More Info
(19 reviews)
Classic Deck Shoe - Blue

Classic Deck Shoe - Blue

£26.50

Typical High Street Price: £94.75

Save £68.25

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

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

Classic Deck Shoe - Navy/Brown

£39.50

Typical High Street Price: £94.75

ANY 2 PAIRS FOR £75

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

More Info
(37 reviews)
Prestige Lightweight Oxford - Brown

Prestige Lightweight Oxford - Brown

£30.00

Typical High Street Price: £93.32

Save £63.32

Prestige lightweight Oxfords in brown at Samuel Windsor. These Lightweight Prestige Collection summer shoes feature an exceptionally light and comfortable sole.

More Info
(9 reviews)
Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

£30.00

Typical High Street Price: £93.32

Save £63.32

Prestige lightweight Derby shoes in tan at Samuel Windsor. These Lightweight Prestige Collection summer shoes feature an exceptionally light and comfortable sole.

More Info
(11 reviews)
Classic Cheltenham Brogue In Suede - Mid Brown

NEW

Classic Cheltenham Brogue In Suede - Mid Brown

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Buy classic suede brogues in light brown from Samuel Windsor. Our handmade suede brogues offer a casual variation on this popular brogue design.

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(3 reviews)
Classic Chichester Shoe - Black

NEW

Classic Chichester Shoe - Black

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

Made using time honoured shoemaking techniques, these handmade five-eyelet Classic Oxford shoes are a traditional Oxford with a modern twist.

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(5 reviews)
Prestige Bartlett Brogue In Suede - Mid Brown

NEW

Prestige Bartlett Brogue In Suede - Mid Brown

£52.50

Typical High Street Price: £129.98

Save £77.48

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

More Info
(1 reviews)
Prestige Suede Chelsea Boot - Black

NEW

Prestige Suede Chelsea Boot - Black

£52.50

Typical High Street Price: £183.00

Save £130.50

These stylish suede Chelsea Boots in black from Samuel Windsor will provide a fantastic complement to your summer casual wardrobe.

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Prestige Country Boot - Black

NEW

Prestige Country Boot - Black

£52.50

Typical High Street Price: £183.00

Save £130.50

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

More Info
(5 reviews)
Prestige Monk Boot - Black

NEW

Prestige Monk Boot - Black

£49.50

Typical High Street Price: £92.50

Save £43.00

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

More Info
Prestige Suede Chelsea Boot - Brown

NEW

Prestige Suede Chelsea Boot - Brown

£52.50

Typical High Street Price: £183.00

Save £130.50

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

More Info
(1 reviews)
Prestige Leyton Boot - Burgundy

NEW

Prestige Leyton Boot - Burgundy

£49.50

Typical High Street Price: £92.50

Save £43.00

Quality men’s leather burgundy boots with a practical rubber sole.

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Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£39.50

Typical High Street Price: £124.33

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
(3682 reviews)
Classic Penny Loafer

Classic Penny Loafer

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

More Info
(1901 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£39.50

Typical High Street Price: £134.74

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
(2209 reviews)
Classic City Shoe - Black

Classic City Shoe - Black

£39.50

Typical High Street Price: £129.98

ANY 2 PAIRS FOR £75

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

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(2672 reviews)
Prestige Oxford Shoe - Rubber Sole - Black

Prestige Oxford Shoe - Rubber Sole - Black

£52.50

Typical High Street Price: £129.98

Save £77.48

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

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(2026 reviews)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

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(1823 reviews)
Classic Kempton Shoe

Classic Kempton Shoe

£39.50

Typical High Street Price: £124.33

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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(2266 reviews)
Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

£47.50

Typical High Street Price: £134.74

Save £87.24

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

More Info
(716 reviews)
Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

£49.50

Typical High Street Price: £183.00

Save £133.50

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

More Info
(1236 reviews)
Prestige Semi-Brogue

Prestige Semi-Brogue

£47.50

Typical High Street Price: £125.99

Save £78.49

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

More Info
(543 reviews)
Classic Penny Loafer

Classic Penny Loafer

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

More Info
(872 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.