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  1. Classic Oxford Shoe
    £32.50 Was £100.00

  2. Classic Cheltenham Brogue
    £32.50 Was £100.00

  3. Classic Penny Loafer Shoe
    £32.50 Was £100.00

  4. Long Sleeve Tattersall Shirt
    £15.00 Was £50.00

  5. Long Sleeve Tattersall Shirt
    £15.00 Was £50.00

  6. Long Sleeve Tattersall Shirt
    £15.00 Was £50.00

  7. Jumbo Cord Trousers
    £20.00 Was £60.00

  8. Prestige Belgravia Boot
    £45.00 Was £115.00

  9. Classic Semi-Brogue
    £32.50 Was £100.00

  10. Jumbo Cord Trousers
    £20.00 Was £60.00

Mens Classic Leather ShoesFROM £27.50

Classic Oxford Shoe - Black

SALE

Classic Oxford Shoe - Black

£32.50 Was £100.00

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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97% (631 reviews)
Classic Cheltenham Brogue - Black

SALE

Classic Cheltenham Brogue - Black

£32.50 Was £100.00

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% (366 reviews)
Classic Penny Loafer Shoe - Black

SALE

Classic Penny Loafer Shoe - Black

£32.50 Was £100.00

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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94% (309 reviews)
Classic Kempton Shoe

SALE

Classic Kempton Shoe

£32.50 Was £100.00

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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96% (193 reviews)
Classic Semi-Brogue - Black

SALE

Classic Semi-Brogue - Black

£32.50 Was £100.00

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

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96% (178 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£32.50 Was £100.00

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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96% (162 reviews)
Classic Monk Shoe - Black

SALE

Classic Monk Shoe - Black

£32.50 Was £100.00

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.

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96% (160 reviews)
Classic Kempton Shoe - Black

SALE

Classic Kempton Shoe - Black

£32.50 Was £100.00

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

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95% (152 reviews)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£32.50 Was £100.00

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

Save £67.50

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91% (149 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£32.50 Was £100.00

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

Save £67.50

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94% (136 reviews)
Classic City Shoe - Black

SALE

Classic City Shoe - Black

£32.50 Was £100.00

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

Save £67.50

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93% (136 reviews)
Classic Quarter-Brogue - Black

SALE

Classic Quarter-Brogue - Black

£32.50 Was £100.00

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

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97% (127 reviews)
Classic Monk Shoe

SALE

Classic Monk Shoe

£32.50 Was £100.00

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

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95% (110 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50 Was £100.00

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

Save £67.50

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95% (100 reviews)
Classic Slip-On Boat Shoe

SALE

Classic Slip-On Boat Shoe

£32.50 Was £100.00

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

Save £67.50

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86% (95 reviews)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£32.50 Was £100.00

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

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97% (94 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£32.50 Was £100.00

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

Save £67.50

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87% (87 reviews)
Classic Sandhurst Shoe - Black

SALE

Classic Sandhurst Shoe - Black

£32.50 Was £100.00

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

Save £67.50

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94% (85 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£32.50 Was £100.00

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

Save £67.50

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93% (85 reviews)
Classic Richmond Shoe - Black

SALE

Classic Richmond Shoe - Black

£32.50 Was £100.00

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

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89% (83 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£32.50 Was £100.00

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

Save £67.50

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97% (79 reviews)
Classic Derby Shoe

SALE

Classic Derby Shoe

£27.50 Was £100.00

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

Save £72.50

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97% (66 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50 Was £100.00

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

Save £67.50

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98% (61 reviews)
Classic Derby Shoe

SALE

Classic Derby Shoe

£27.50 Was £100.00

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

Save £72.50

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96% (56 reviews)
Classic Durham Shoe

SALE

Classic Durham Shoe

£32.50 Was £100.00

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

Save £67.50

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89% (53 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£27.50 Was £100.00

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

Save £72.50

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92% (50 reviews)
Classic Leather Lace-Up Trainer

SALE

Classic Leather Lace-Up Trainer

£32.50 Was £100.00

Classic Leather Trainer Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £67.50

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90% (48 reviews)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£32.50 Was £100.00

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

Save £67.50

More Info
95% (91 reviews)
Classic Lace-Up Boat Shoe

SALE

Classic Lace-Up Boat Shoe

£32.50 Was £100.00

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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97% (36 reviews)
Classic Claridge Shoe - Black

SALE

Classic Claridge Shoe - Black

£32.50 Was £100.00

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

Save £67.50

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85% (33 reviews)
Classic Oxford Shoe - Cigar

SALE

Classic Oxford Shoe - Cigar

£32.50 Was £100.00

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

Save £67.50

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96% (118 reviews)
Classic Quarter-Brogue

SALE

Classic Quarter-Brogue

£32.50 Was £100.00

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

Save £67.50

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89% (74 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50 Was £100.00

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

Save £67.50

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80% (152 reviews)
Classic Leather Touch Fastening Trainer

SALE

Classic Leather Touch Fastening Trainer

£32.50 Was £100.00

Classic Leather Trainer, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £67.50

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94% (16 reviews)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£32.50 Was £100.00

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

Save £67.50

More Info
94% (70 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.

Our 'was' pricing refers to the original selling prices offered on our website www.swshoes.co.uk, and in our retail store between November 01 2015 and February 02 2016 (items sold at 'was' prices represent the lower proportion of sales).