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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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(3689 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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(7144 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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(1569 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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(2055 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.

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(1394 reviews)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

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(1166 reviews)
Classic Sandhurst Shoe - Black

SALE

Classic Sandhurst Shoe - Black

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

More Info
(307 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.

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(568 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£26.00

Typical High Street Price: £89.75

Save £63.75

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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(67 reviews)
Classic Derby Shoe

SALE

Classic Derby Shoe

£26.00

Typical High Street Price: £128.00

Save £102.00

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

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(318 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
(282 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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(323 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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(141 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£39.50

Typical High Street Price: £120.75

ANY 2 PAIRS FOR £75

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

More Info
(129 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£26.00

Typical High Street Price: £89.75

Save £63.75

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 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
(90 reviews)
Classic Monk Brogue - Black

SALE

Classic Monk Brogue - Black

£39.50

Typical High Street Price: £119.33

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.

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(140 reviews)
Classic Cheltenham Brogue in Suede

SALE

Classic Cheltenham Brogue in Suede

£39.50

Typical High Street Price: £120.75

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.

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(72 reviews)
Classic Cheltenham Brogue

SALE

Classic Cheltenham Brogue

£39.50

Typical High Street Price: £120.75

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.

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(79 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
(50 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.

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(47 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.

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(17 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.

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(3626 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
(1877 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
(2169 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)
Classic Cheltenham Brogue - Black

SALE

Classic Cheltenham Brogue - Black

£39.50

Typical High Street Price: £120.75

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.

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(2714 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
(1786 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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(2223 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
(858 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.