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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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(7208 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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(1504 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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(1404 reviews)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£49.95

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £85

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

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(1178 reviews)
Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

£35.95

Typical High Street Price: £128.50

Save £92.55

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

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(315 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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(579 reviews)
Classic Deck Shoe

Classic Deck Shoe

£34.95

Typical High Street Price: £92.25

Save £57.30

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

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(69 reviews)
Classic Derby Shoe

Classic Derby Shoe

£49.95

Typical High Street Price: £128.00

Save £78.05

Classic Derby Shoe - Blue, online from Samuel Windsor. Tailored quality at outstanding prices.

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(318 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)
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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(332 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)
Classic Oxford Shoe

Classic Oxford Shoe

£49.95

Typical High Street Price: £133.25

ANY 2 PAIRS FOR £85

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

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(132 reviews)
Classic Driving Shoe

Classic Driving Shoe

£49.95

Typical High Street Price: £75.00

ANY 2 PAIRS FOR £85

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

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(71 reviews)
Classic Moccasin

Classic Moccasin

£49.95

Typical High Street Price: £75.00

ANY 2 PAIRS FOR £85

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

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(68 reviews)
Classic Deck Shoe

Classic Deck Shoe

£34.95

Typical High Street Price: £92.25

Save £57.30

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

More Info
(54 reviews)
Classic Monk Brogue - Black

Classic Monk Brogue - Black

£49.95

Typical High Street Price: £136.00

ANY 2 PAIRS FOR £85

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.

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(161 reviews)
Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

£49.95

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £85

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

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(75 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£49.95

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £85

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

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(82 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.

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(86 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.

More Info
(70 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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(30 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.

More Info
(1 reviews)
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 Driving Shoe

NEW

Classic Driving Shoe

£49.95

Typical High Street Price: £75.00

ANY 2 PAIRS FOR £85

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

More Info
(2 reviews)
Classic Moccasin - Brown

NEW

Classic Moccasin - Brown

£49.95

Typical High Street Price: £75.00

ANY 2 PAIRS FOR £85

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

More Info
(1 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
(6 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.

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(3651 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
(1888 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.

More Info
(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)
Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

£49.95

Typical High Street Price: £128.50

ANY 2 PAIRS FOR £85

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.

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(2739 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.

More Info
(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)
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)

Our classic shoes collection features both formal and casual designs. Samuel Windsor's traditional shoe styles include classic tan Sandhurst shoes, formal chestnut brown Oxfords, brown suede penny loafers and casual blue deck shoes. Order your classic leather and suede shoes today. Available in UK sizes 5 to 14.