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Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(3729 reviews)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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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(7323 reviews)
Classic Semi-Brogue

Classic Semi-Brogue

$69.00
Was $135.00

Buy 2 pairs for $130

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

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(1608 reviews)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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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(2099 reviews)
Classic Monk Shoe

Classic Monk Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(1429 reviews)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(1196 reviews)
Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

$79.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(316 reviews)
Classic Penny Loafer

Classic Penny Loafer

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(327 reviews)
Classic Deck Shoe

Classic boat Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(610 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(309 reviews)
Classic Slip-On Deck Shoe

Classic Slip-On boat Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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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(354 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(142 reviews)
Classic Monk Brogue - Black

Classic Monk Brogue - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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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(183 reviews)
Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(89 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

$69.00
Was $135.00

Buy 2 pairs for $130

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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(106 reviews)
Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(141 reviews)
Classic Monk Shoe

Classic Monk Shoe

$59.00
Was $135.00

Save $76.00

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

$69.00
Was $135.00

Buy 2 pairs for $130

More Info
(28 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

$69.00
Was $135.00

Buy 2 pairs for $130

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
(124 reviews)
Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(44 reviews)
Classic Deck Shoe - Tobacco

Classic boat Shoe - Tobacco

$59.00
Was $135.00

Save $76.00

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

More Info
(21 reviews)
Classic Deck Shoe - Blue

Classic boat Shoe - Blue

$59.00
Was $135.00

Save $76.00

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 boat Shoe - Navy/Brown

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(38 reviews)
Classic Cheltenham Brogue In Suede - Mid Brown

NEW

Classic Cheltenham Brogue In Suede - Mid Brown

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(7 reviews)
Classic Chichester Shoe - Black

NEW

Classic Chichester Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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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(8 reviews)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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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(3690 reviews)
Classic Penny Loafer

Classic Penny Loafer

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(1904 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

Crafted using time honoured shoe making techniques, these Samuel Windsor Classic Oxford Shoes in chestnut brown are classic formal shoes or office shoes.

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(2214 reviews)
Classic City Shoe - Black

Classic City Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(2673 reviews)
Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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
(2794 reviews)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(1827 reviews)
Classic Kempton Shoe

Classic Kempton Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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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(2267 reviews)
Classic Penny Loafer

Classic Penny Loafer

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(873 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.