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  1. Classic Oxford Shoe - Black £35.00

  2. Prestige Oxford Shoe - Black - Rubber Sole £45.00

  3. Classic Cheltenham Brogue - Black £35.00

  4. Classic Penny Loafer Shoe - Black £35.00

  5. Covert Coat - Fawn £149.00

  6. Prestige Chelsea Boot - Black £45.00

  7. Prestige Semi-Brogue - Black £45.00

  8. Prestige Chelsea Boot - Brown Suede £45.00

  9. Classic City Shoe - Black £35.00

  10. Prestige Chelsea Boot - Brown £45.00

Mens Classic Leather ShoesONLY £35.00

Classic Oxford Shoe - Tan More Info

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Classic Oxford Shoe - Tan

£35.00 WAS £100

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

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12 reviews

Classic Sandhurst Shoe - Brown More Info

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Classic Sandhurst Shoe - Brown

£35.00 WAS £100

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

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3 reviews

Classic Semi-Brogue - Brown More Info

NEW

Classic Semi-Brogue - Brown

£35.00 WAS £100

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

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3 reviews

Classic Quarter-Brogue - Brown More Info

NEW

Classic Quarter-Brogue - Brown

£35.00 WAS £100

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

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5 reviews

Classic Oxford Shoe - Brown More Info

NEW

Classic Oxford Shoe - Brown

£35.00 WAS £100

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

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2 reviews

Classic Deck Shoe - Navy More Info

Classic Deck Shoe - Navy

£35.00 WAS £100

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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28 reviews

Classic Deck Shoe - Nubuck More Info

Classic Deck Shoe - Nubuck

£35.00 WAS £100

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

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25 reviews

Classic Derby Shoe - Tobacco More Info

Classic Derby Shoe - Tobacco

£35.00 WAS £100

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

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55 reviews

Classic Derby Shoe - Blue More Info

Classic Derby Shoe - Blue

£35.00 WAS £100

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

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60 reviews

Classic Penny Loafer - Dark Brown Suede More Info

Classic Penny Loafer - Dark Brown Suede

£35.00 WAS £100

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

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61 reviews

Classic Royal Brogue - Brown Suede More Info

Classic Royal Brogue - Brown Suede

£35.00 WAS £100

Classic Royal Brogue - Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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104 reviews

Classic Deck Shoe - Brown More Info

Classic Deck Shoe - Brown

£35.00 WAS £100

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

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133 reviews

Classic Claridge Shoe - Black More Info

Classic Claridge Shoe - Black

£35.00 WAS £100

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

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45 reviews

Classic Durham Shoe - Tan More Info

Classic Durham Shoe - Tan

£35.00 WAS £100

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

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71 reviews

Classic Deck Shoe - Blue/Brown More Info

Classic Deck Shoe - Blue/Brown

£35.00 WAS £100

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

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74 reviews

Classic Deck Shoe - Blue/Brown/White More Info

Classic Deck Shoe - Blue/Brown/White

£35.00 WAS £100

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

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no reviews

Classic Deck Shoe - Nubuck More Info

Classic Deck Shoe - Nubuck

£35.00 WAS £100

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

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56 reviews

Classic Gibson Shoe - Black More Info

Classic Gibson Shoe - Black

£35.00 WAS £100

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

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98 reviews

Classic Sandhurst Shoe - Black More Info

Classic Sandhurst Shoe - Black

£35.00 WAS £100

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

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59 reviews

Classic Leather Trainer - Brown More Info

Classic Leather Trainer - Brown

£35.00 WAS £100

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

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74 reviews

Classic Camden Shoe More Info

Classic Camden Shoe

£35.00 WAS £100

Classic Camden Shoe, online from Samuel Windsor. Tailored quality at outstanding prices.

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19 reviews

Classic Sandhurst Shoe - Tan More Info

Classic Sandhurst Shoe - Tan

£35.00 WAS £100

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

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243 reviews

Classic Leather Trainer More Info

Classic Leather Trainer

£35.00 WAS £100

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

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37 reviews

Classic Penny Loafer - Brown Suede More Info

Classic Penny Loafer - Brown Suede

£35.00 WAS £100

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

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104 reviews

Classic Oxford Shoe - Black More Info

Classic Oxford Shoe - Black

£35.00 WAS £100

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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453 reviews

Classic Kempton Shoe - Black More Info

Classic Kempton Shoe - Black

£35.00 WAS £100

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

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127 reviews

Classic Kempton Shoe - Burgundy More Info

Classic Kempton Shoe - Burgundy

£35.00 WAS £100

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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153 reviews

Classic Penny Loafer Shoe - Black More Info

Classic Penny Loafer Shoe - Black

£35.00 WAS £100

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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299 reviews

Classic Monk Shoe - Burgundy-Brown More Info

Classic Monk Shoe - Burgundy-Brown

£35.00 WAS £100

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

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135 reviews

Classic Richmond Shoe - Black More Info

Classic Richmond Shoe - Black

£35.00 WAS £100

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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57 reviews

Classic Cheltenham Brogue - Black More Info

Classic Cheltenham Brogue - Black

£35.00 WAS £100

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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367 reviews

Classic Semi-Brogue - Brown Suede More Info

Classic Semi-Brogue - Brown Suede

£35.00 WAS £100

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

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80 reviews

Classic Penny Loafer - Chestnut Brown More Info

Classic Penny Loafer - Chestnut Brown

£35.00 WAS £100

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

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128 reviews

Classic Semi-Brogue - Black More Info

Classic Semi-Brogue - Black

£35.00 WAS £100

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

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153 reviews

Classic City Shoe - Black More Info

Classic City Shoe - Black

£35.00 WAS £100

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

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218 reviews

Classic Oxford Shoe - Chestnut Brown More Info

Classic Oxford Shoe - Chestnut Brown

£35.00 WAS £100

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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218 reviews

Classic Monk Shoe -  Black More Info

Classic Monk Shoe - Black

£35.00 WAS £100

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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172 reviews

Classic Quarter-Brogue - Black More Info

Classic Quarter-Brogue - Black

£35.00 WAS £100

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

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116 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.