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Classic Semi-Brogue - Black

SALE

Classic Semi-Brogue - Black

£39.95

Typical High Street Price: £129.75

ANY 2 PAIRS FOR £75

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

More Info
(3719 reviews)
Classic Oxford Shoe - Black

SALE

Classic Oxford Shoe - Black

£39.95

Typical High Street Price: £134.50

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.

More Info
(7282 reviews)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£39.95

Typical High Street Price: £129.75

ANY 2 PAIRS FOR £75

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

More Info
(1513 reviews)
Classic Quarter-Brogue - Black

SALE

Classic Quarter-Brogue - Black

£39.95

Typical High Street Price: £129.75

ANY 2 PAIRS FOR £75

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

More Info
(1593 reviews)
Classic Monk Shoe - Black

SALE

Classic Monk Shoe - Black

£39.95

Typical High Street Price: £127.67

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.

More Info
(2086 reviews)
Classic Monk Shoe

SALE

Classic Monk Shoe

£39.95

Typical High Street Price: £127.67

ANY 2 PAIRS FOR £75

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

More Info
(1419 reviews)
Prestige Tasselled Loafer - Black

SALE

Prestige Tasselled Loafer - Black

£47.50

Typical High Street Price: £127.67

Save £80.17

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

More Info
(531 reviews)
Prestige Brogue - Rubber Sole - Black

SALE

Prestige Brogue - Rubber Sole - Black

£52.50

Typical High Street Price: £129.67

Save £77.17

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

More Info
(473 reviews)
Prestige Brogue - Rubber Sole

SALE

Prestige Brogue - Rubber Sole

£52.50

Typical High Street Price: £129.67

Save £77.17

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

More Info
(662 reviews)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£39.95

Typical High Street Price: £129.75

ANY 2 PAIRS FOR £75

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

More Info
(1188 reviews)
Prestige Tasselled Suede Loafer

SALE

Prestige Tasselled Suede Loafer

£47.50

Typical High Street Price: £127.67

Save £80.17

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

More Info
(262 reviews)
Prestige Country Brogue - Rubber Sole

SALE

Prestige Country Brogue - Rubber Sole

£52.50

Typical High Street Price: £129.75

Save £77.25

Prestige Country Brogue - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

More Info
(294 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£39.95

Typical High Street Price: £127.67

ANY 2 PAIRS FOR £75

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

More Info
(321 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£39.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £75

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

More Info
(602 reviews)
Prestige Penny Loafer - Black

SALE

Prestige Penny Loafer - Black

£47.50

Typical High Street Price: £127.67

Save £80.17

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

More Info
(253 reviews)
Prestige Penny Loafer

SALE

Prestige Penny Loafer

£47.50

Typical High Street Price: £127.67

Save £80.17

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

More Info
(207 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£39.95

Typical High Street Price: £134.50

ANY 2 PAIRS FOR £75

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

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

SALE

Prestige Slip-On Deck Shoe

£47.50

Typical High Street Price: £118.50

Save £71.00

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

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

SALE

Prestige Slip-On Deck Shoe

£47.50

Typical High Street Price: £118.50

Save £71.00

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.

More Info
(297 reviews)
Prestige Cumbria Boot

SALE

Prestige Cumbria Boot

£49.50

Typical High Street Price: £87.50

Save £38.00

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.

More Info
(136 reviews)
Prestige Leather Lace-Up Deck Shoe

SALE

Prestige Leather Lace-Up Deck Shoe

£47.50

Typical High Street Price: £118.50

Save £71.00

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

More Info
(347 reviews)
Prestige Lace-Up Deck Shoe

SALE

Prestige Lace-Up Deck Shoe

£47.50

Typical High Street Price: £118.50

Save £71.00

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.

More Info
(200 reviews)
Prestige Deck Shoe

SALE

Prestige Deck Shoe

£47.50

Typical High Street Price: £118.50

Save £71.00

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

More Info
(181 reviews)
Prestige Dress Shoe - Black

SALE

Prestige Dress Shoe - Black

£47.50

Typical High Street Price: £107.50

Save £60.00

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.

More Info
(188 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£39.95

Typical High Street Price: £134.50

ANY 2 PAIRS FOR £75

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

More Info
(137 reviews)
Prestige Belgravia Shoe

SALE

Prestige Belgravia Shoe

£49.50

Typical High Street Price: £87.50

Save £38.00

These nubuck men’s boots are a great addition to any gent’s wardrobe.

More Info
(156 reviews)
Prestige Chelsea Boot

SALE

Prestige Chelsea Boot

£49.50

Typical High Street Price: £175.00

Save £125.50

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

More Info
(252 reviews)
Classic Driving Shoe

SALE

Classic Driving Shoe

£39.95

Typical High Street Price: £80.50

ANY 2 PAIRS FOR £75

Classic Driving Shoe are comfortable to wear which is perfect for the summer.

More Info
(80 reviews)
Classic Moccasin

SALE

Classic Moccasin

£39.95

Typical High Street Price: £80.50

ANY 2 PAIRS FOR £75

Made from the finest, soft Italian leather, our Classic moccasins are carefully hand stitched, creating a wonderfully comfortable and durable casual shoe.

More Info
(81 reviews)
Prestige Oxford - Black

SALE

Prestige Oxford - Black

£49.50

Typical High Street Price: £151.33

Save £101.83

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

More Info
(155 reviews)
Prestige Split Brogue

SALE

Prestige Split Brogue

£49.50

Typical High Street Price: £151.33

Save £101.83

Make an entrance with Samuel Windsor Prestige Split Brogues. Its two-tone style and punch detailing make for an outstanding finish.

More Info
(131 reviews)
Prestige Twin Monk - Black

SALE

Prestige Twin Monk - Black

£47.50

Typical High Street Price: £127.67

Save £80.17

Prestige Twin Monk, online from Samuel Windsor. Tailored quality at outstanding prices.

More Info
(104 reviews)
Prestige Brogue - Black

SALE

Prestige Brogue - Black

£49.50

Typical High Street Price: £151.33

Save £101.83

Prestige Black Brogues, online from Samuel Windsor. Tailored quality at outstanding prices.

More Info
(122 reviews)
Classic Monk Brogue - Black

SALE

Classic Monk Brogue - Black

£39.95

Typical High Street Price: £127.67

ANY 2 PAIRS FOR £75

These monk brogue shoes have been producted using the finest Italian leathers and using a goodyear welted construction which offers and unbeatable combination of durability and comfort and an exceptional price.

More Info
(177 reviews)
Classic Cheltenham Brogue in Suede

SALE

Classic Cheltenham Brogue in Suede

£39.95

Typical High Street Price: £129.75

ANY 2 PAIRS FOR £75

Buy classic suede brogues from Samuel Windsor. Our handmade suede brogues offer a casual variation of this classic brogue design.

More Info
(84 reviews)
Classic Cheltenham Brogue

SALE

Classic Cheltenham Brogue

£39.95

Typical High Street Price: £129.75

ANY 2 PAIRS FOR £75

Buy classic leather brogues. Our handmade tan leather brogues are stylish and comfortable, treading the line perfectly between smart and casual.

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

SALE

Prestige Oxford Dress Shoe - Black

£47.50

Typical High Street Price: £107.50

Save £60.00

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

More Info
(69 reviews)
Prestige Penny Loafer Suede - Navy

SALE

Prestige Penny Loafer Suede - Navy

£49.50

Typical High Street Price: £127.67

Save £78.17

Classic Black Suede Penny loafers from Samuel Windsor. Visit now for outstanding offers.

More Info
(43 reviews)
Prestige Penny Loafer Suede - Brown

SALE

Prestige Penny Loafer Suede - Brown

£49.50

Typical High Street Price: £127.67

Save £78.17

Classic Brown Suede Penny loafers from Samuel Windsor. Visit now for outstanding offers.

More Info
(35 reviews)
Classic Oxford Shoe - Oxblood

SALE

Classic Oxford Shoe - Oxblood

£39.95

Typical High Street Price: £134.50

ANY 2 PAIRS FOR £75

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

More Info
(117 reviews)
Classic Monk Shoe

SALE

Classic Monk Shoe

£39.95

Typical High Street Price: £127.67

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
(22 reviews)
Classic Cheltenham Brogue

SALE

Classic Cheltenham Brogue

£39.95

Typical High Street Price: £129.75

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
(93 reviews)
Classic Suede Oxford Shoe

SALE

Classic Suede Oxford Shoe

£39.95

Typical High Street Price: £134.50

ANY 2 PAIRS FOR £75

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

More Info
(42 reviews)
Prestige Whitworth Brogue

SALE

Prestige Whitworth Brogue

£49.50

Typical High Street Price: £151.33

Save £101.83

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

More Info
(70 reviews)
Prestige Whitworth Brogue - Black

SALE

Prestige Whitworth Brogue - Black

£49.50

Typical High Street Price: £151.33

Save £101.83

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

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

SALE

Prestige Twin Monk Shoe - Oxblood

£47.50

Typical High Street Price: £127.67

Save £80.17

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

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

SALE

Prestige Oxford Shoe - Rubber Sole

£52.50

Typical High Street Price: £129.67

Save £77.17

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

More Info
(12 reviews)
Prestige Split Brogue

SALE

Prestige Split Brogue

£49.50

Typical High Street Price: £151.33

Save £101.83

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
(30 reviews)
Prestige Bartlett Brogue

SALE

Prestige Bartlett Brogue

£52.50

Typical High Street Price: £129.67

Save £77.17

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

More Info
(37 reviews)
Prestige Bartlett Brogue

SALE

Prestige Bartlett Brogue

£52.50

Typical High Street Price: £129.67

Save £77.17

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

More Info
(9 reviews)
Classic Deck Shoe - Tobacco

SALE

Classic Deck Shoe - Tobacco

£39.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £75

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

More Info
(10 reviews)
Classic Deck Shoe - Blue

SALE

Classic Deck Shoe - Blue

£39.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £75

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

More Info
(13 reviews)
Classic Driving Shoe

SALE

Classic Driving Shoe

£39.95

Typical High Street Price: £80.50

ANY 2 PAIRS FOR £75

Classic Driving Shoe are comfortable to wear which is perfect for the summer.

More Info
(21 reviews)
Classic Moccasin - Brown

SALE

Classic Moccasin - Brown

£39.95

Typical High Street Price: £80.50

ANY 2 PAIRS FOR £75

Made from the finest, soft Italian leather, our Classic moccasins are carefully hand stitched, creating a wonderfully comfortable and durable casual shoe.

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

SALE

Classic Deck Shoe - Navy/Brown

£39.95

Typical High Street Price: £92.25

ANY 2 PAIRS FOR £75

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

More Info
(32 reviews)
Prestige Lightweight Oxford - Brown

SALE

Prestige Lightweight Oxford - Brown

£47.50

Typical High Street Price: £85.00

Save £37.50

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

More Info
(5 reviews)
Prestige Lightweight Brogue - Navy

SALE

Prestige Lightweight Brogue - Navy

£47.50

Typical High Street Price: £85.00

Save £37.50

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

More Info
(6 reviews)
Prestige Lightweight Brogue - Sand

SALE

Prestige Lightweight Brogue - Sand

£47.50

Typical High Street Price: £85.00

Save £37.50

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

More Info
(8 reviews)
Prestige Penny Loafer - Suede - Black

SALE

Prestige Penny Loafer - Suede - Black

£49.50

Typical High Street Price: £127.67

Save £78.17

Classic Black Suede Penny loafers from Samuel Windsor. Visit now for outstanding offers.

More Info
Prestige Tasselled Loafer - Sand

SALE

Prestige Tasselled Loafer - Sand

£47.50

Typical High Street Price: £127.67

Save £80.17

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

More Info
(5 reviews)
Prestige Suede Chelsea Boot - Navy

SALE

Prestige Suede Chelsea Boot - Navy

£49.50

Typical High Street Price: £87.50

Save £38.00

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

More Info
(7 reviews)
Prestige Suede Chelsea Boot - Sand

SALE

Prestige Suede Chelsea Boot - Sand

£49.50

Typical High Street Price: £87.50

Save £38.00

These stylish Prestige Suede Chelsea Boot - Sand, from Samuel Windsor will provide a fantastic complement to your summer casual wardrobe.

More Info
(3 reviews)
Prestige Lightweight Derby - Tan

SALE

Prestige Lightweight Derby - Tan

£47.50

Typical High Street Price: £85.00

Save £37.50

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

More Info
(7 reviews)
Prestige Driving Shoe - Navy/Brown

SALE

Prestige Driving Shoe - Navy/Brown

£47.50

Typical High Street Price: £118.50

Save £71.00

Made from the finest, super-soft Italian Nubuck leather, our two-tone Prestige driving shoes are carefully handmade using genuine moccasin stitching

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

SALE

Classic Penny Loafer Shoe - Black

£39.95

Typical High Street Price: £127.67

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
(3671 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£39.95

Typical High Street Price: £127.67

ANY 2 PAIRS FOR £75

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

More Info
(1899 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£39.95

Typical High Street Price: £134.50

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
(2199 reviews)
Classic City Shoe - Black

SALE

Classic City Shoe - Black

£39.95

Typical High Street Price: £129.67

ANY 2 PAIRS FOR £75

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

More Info
(2668 reviews)
Prestige Oxford Shoe - Rubber Sole - Black

SALE

Prestige Oxford Shoe - Rubber Sole - Black

£52.50

Typical High Street Price: £129.67

Save £77.17

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

More Info
(2019 reviews)
Classic Cheltenham Brogue - Black

SALE

Classic Cheltenham Brogue - Black

£39.95

Typical High Street Price: £129.75

ANY 2 PAIRS FOR £75

Buy classic black brogues. A staple shoe for the modern man, our handmade classic cheltenham brogues are the perfect shoe for formal and casual occasions.

More Info
(2771 reviews)
Classic Kempton Shoe - Black

SALE

Classic Kempton Shoe - Black

£39.95

Typical High Street Price: £127.67

ANY 2 PAIRS FOR £75

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

More Info
(1816 reviews)
Classic Kempton Shoe

SALE

Classic Kempton Shoe

£39.95

Typical High Street Price: £127.67

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.

More Info
(2251 reviews)
Prestige Oxford Shoe - Black

SALE

Prestige Oxford Shoe - Black

£47.50

Typical High Street Price: £134.50

Save £87.00

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

More Info
(714 reviews)
Prestige Chelsea Boot - Black

SALE

Prestige Chelsea Boot - Black

£49.50

Typical High Street Price: £175.00

Save £125.50

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

More Info
(1226 reviews)
Prestige Suede Chelsea Boot

SALE

Prestige Suede Chelsea Boot

£49.50

Typical High Street Price: £175.00

Save £125.50

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

More Info
(657 reviews)
Prestige Semi-Brogue - Black

SALE

Prestige Semi-Brogue - Black

£47.50

Typical High Street Price: £129.75

Save £82.25

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

More Info
(799 reviews)
Prestige Semi-Brogue

SALE

Prestige Semi-Brogue

£47.50

Typical High Street Price: £129.75

Save £82.25

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

More Info
(540 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£39.95

Typical High Street Price: £127.67

ANY 2 PAIRS FOR £75

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

More Info
(871 reviews)

Too many shoes to choose from? Ask yourself a few questions, and refine your choice. Are you looking for brown or black shoes? Do you want lace up or slip-on shoes? Are you looking for a particular style, maybe Oxfords, Brogues, Chelsea boots or leather loafers? If you know the answer to any of these questions, click the main menu at the top, choose shoes, and select the colour or style you're searching for.