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95%
104,040 Reviews

Most Popular

  1. Classic Oxford Shoe
    £35.00

  2. Classic Penny Loafer Shoe
    £35.00

  3. Classic Cheltenham Brogue
    £35.00

  4. Outdoor Mule
    £30.00

  5. Classic Deck Shoe
    £32.50

  6. Classic Oxford Shoe
    £35.00

  7. Classic Sandhurst Shoe
    £35.00

  8. Classic Kempton Shoe
    £35.00

  9. Classic Quarter-Brogue
    £35.00

  10. Classic Monk Shoe
    £35.00

Mens Classic Leather ShoesFROM £25.00

Classic Penny Loafer Shoe - Black

SALE

Classic Penny Loafer Shoe - Black

£35.00

Typical High Street Price: £127.67

These black Penny Loafer men's leather shoes from Samuel Windsor are classic formal shoes combined with supple, easy slip-on access.

Save £92.67

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92% (506 reviews)
Classic Oxford Shoe - Black

SALE

Classic Oxford Shoe - Black

£35.00

Typical High Street Price: £124.75

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.

Save £89.75

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96% (959 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £127.67

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

Save £92.67

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92% (226 reviews)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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94% (224 reviews)
Classic Kempton Shoe

SALE

Classic Kempton Shoe

£35.00

Typical High Street Price: £127.67

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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97% (392 reviews)
Classic Cheltenham Brogue - Black

SALE

Classic Cheltenham Brogue - Black

£35.00

Typical High Street Price: £134.75

Cheltenham Half Brogues mens leather shoes, formal shoes or office shoes, mens brogue shoes which retain the elegant craftmanship personified by hand-stitching.

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95% (546 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£35.00

Typical High Street Price: £124.75

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

Save £89.75

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95% (274 reviews)
Classic Monk Shoe - Black

SALE

Classic Monk Shoe - Black

£35.00

Typical High Street Price: £131.00

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.

Save £96.00

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96% (262 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£35.00

Typical High Street Price: £124.75

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

Save £89.75

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98% (132 reviews)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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98% (133 reviews)
Classic Monk Shoe

SALE

Classic Monk Shoe

£35.00

Typical High Street Price: £131.00

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

Save £96.00

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96% (182 reviews)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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98% (54 reviews)
Classic City Shoe - Black

SALE

Classic City Shoe - Black

£35.00

Typical High Street Price: £127.00

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

Save £92.00

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93% (126 reviews)
Classic Slip-On Deck Shoe

SALE

Classic Slip-On Deck Shoe

£32.50

Typical High Street Price: £88.50

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

Save £56.00

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89% (124 reviews)
Classic Lace-Up Deck Shoe

SALE

Classic Lace-Up Deck Shoe

£32.50

Typical High Street Price: £88.50

Our Classic Lace-Up Boat Shoes are handmade by Samuel Windsor. These designer lace-up shoes are crafted using only the finest leathers.

Save £56.00

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91% (34 reviews)
Classic Oxford Shoe - Cigar

SALE

Classic Oxford Shoe - Cigar

£35.00

Typical High Street Price: £124.75

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

Save £89.75

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94% (126 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50

Typical High Street Price: £88.50

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

Save £56.00

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99% (87 reviews)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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99% (73 reviews)
Classic Quarter-Brogue

SALE

Classic Quarter-Brogue

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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94% (54 reviews)
Classic Moccasin

SALE

Classic Moccasin

£32.50

Typical High Street Price: £62.50

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

Save £30.00

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100% (58 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50

Typical High Street Price: £88.50

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

Save £56.00

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100% (43 reviews)
Nubuck Trainer - Earth Sole

SALE

Nubuck Trainer - Earth Sole

£25.00

Nubuck Trainer - Earth Sole, online from Samuel Windsor. Tailored quality at outstanding prices.

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95% (40 reviews)
Casual lace-up

SALE

Casual lace-up

£25.00

Casual Lace Up shoes, online from Samuel Windsor. Tailored quality at outstanding prices.

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95% (19 reviews)
Classic Driving Shoe

SALE

Classic Driving Shoe

£32.50

Typical High Street Price: £62.50

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

Save £30.00

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91% (70 reviews)
Classic Durham Shoe

SALE

Classic Durham Shoe

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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89% (61 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £127.67

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

Save £92.67

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87% (109 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50

Typical High Street Price: £88.50

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

Save £56.00

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96% (147 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£35.00

Typical High Street Price: £88.50

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

Save £53.50

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80% (152 reviews)
Classic Sandhurst Shoe - Black

SALE

Classic Sandhurst Shoe - Black

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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94% (113 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £127.67

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

Save £92.67

More Info
94% (124 reviews)
Classic Semi-Brogue - Black

SALE

Classic Semi-Brogue - Black

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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97% (228 reviews)
Classic Quarter-Brogue - Black

SALE

Classic Quarter-Brogue - Black

£35.00

Typical High Street Price: £134.75

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

Save £99.75

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98% (163 reviews)
Classic Richmond Shoe - Black

SALE

Classic Richmond Shoe - Black

£35.00

Typical High Street Price: £127.00

Great office shoes, these Samuel Windsor Richmond Classics mens black shoes are handmade, incorporating a leather lining which is both breathable and seamless.

Save £92.00

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89% (104 reviews)
Classic Kempton Shoe - Black

SALE

Classic Kempton Shoe - Black

£35.00

Typical High Street Price: £127.67

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

Save £92.67

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95% (215 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 in sizes 5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 12, 13, and 14.