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  1. Black Oxford Shoes £44.95

  2. Classic Cheltenham Brogues - Black £44.95

  3. Classic Penny Loafer Shoe - Black £44.95

  4. Classic Sandhurst Shoe - Tan £44.95

  5. Classic City Shoe - Black £44.95

  6. Prestige Semi-Brogue - Black - Italian Leather Upper £59.95

  7. Classic Oxford Shoes - Chestnut Brown £44.95

  8. Moleskin Jacket - Tan £59.00

  9. Classic Penny Loafer Suede £44.95

  10. Classic Deck Shoe - Brown £44.95

Black Oxford Shoes More Info

Black Oxford Shoes

£44.95 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.

Buy any 2 pairs for £75

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424 reviews

Classic Cheltenham Brogues - Black More Info

Classic Cheltenham Brogues - Black

£44.95 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.

Buy any 2 pairs for £75

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238 reviews

Classic Penny Loafer Shoe - Black More Info

Classic Penny Loafer Shoe - Black

£44.95 WAS £100

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

Buy any 2 pairs for £75

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284 reviews

Classic Semi-Brogues - Black More Info

Classic Semi-Brogues - Black

£44.95 WAS £100

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

Buy any 2 pairs for £75

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201 reviews

Classic Oxford Shoes - Chestnut Brown More Info

Classic Oxford Shoes - Chestnut Brown

£44.95 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.

Buy any 2 pairs for £75

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144 reviews

Classic Monk Shoes - Black More Info

Classic Monk Shoes - Black

£44.95 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.

Buy any 2 pairs for £75

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153 reviews

Classic City Shoe - Black More Info

Classic City Shoe - Black

£44.95 WAS £100

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

Buy any 2 pairs for £75

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234 reviews

Classic Sandhurst Shoe - Tan More Info

Classic Sandhurst Shoe - Tan

£44.95 WAS £100

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

Buy any 2 pairs for £75

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223 reviews

Classic Royal Brogue - Brown Suede More Info

Classic Royal Brogue - Brown Suede

£44.95 WAS £100

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

Buy any 2 pairs for £75

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85 reviews

Classic Derby Shoe - Tobacco More Info

NEW

Classic Derby Shoe - Tobacco

£44.95 WAS £100

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

Buy any 2 pairs for £75

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8 reviews

Classic Penny Loafer Suede More Info

Classic Penny Loafer Suede

£44.95 WAS £100

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

Buy any 2 pairs for £75

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135 reviews

Classic Deck Shoe - Brown More Info

Classic Deck Shoe - Brown

£44.95 WAS £100

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

Buy any 2 pairs for £75

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55 reviews

Classic Kempton Burgundy Shoe - Slip-On More Info

Classic Kempton Burgundy Shoe - Slip-On

£44.95 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.

Buy any 2 pairs for £75

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119 reviews

Classic Plain Toe Cap Quarter Brogue - Black More Info

Classic Plain Toe Cap Quarter Brogue - Black

£44.95 WAS £100

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

Buy any 2 pairs for £75

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105 reviews

Classic Leather Trainer Brown More Info

Classic Leather Trainer Brown

£44.95 WAS £100

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

Buy any 2 pairs for £75

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77 reviews

Classic Kempton Black Shoe - Slip-On More Info

Classic Kempton Black Shoe - Slip-On

£44.95 WAS £100

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

Buy any 2 pairs for £75

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133 reviews

Classic Gibson - Black More Info

Classic Gibson - Black

£44.95 WAS £100

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

Buy any 2 pairs for £75

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114 reviews

Classic Penny Loafer - Dark Brown Suede More Info

Classic Penny Loafer - Dark Brown Suede

£44.95 WAS £100

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

Buy any 2 pairs for £75

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37 reviews

Classic Suede Semi-Brogues - Brown Suede More Info

Classic Suede Semi-Brogues - Brown Suede

£44.95 WAS £100

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

Buy any 2 pairs for £75

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87 reviews

Classic Penny Loafer Shoe - Chestnut Brown More Info

Classic Penny Loafer Shoe - Chestnut Brown

£44.95 WAS £100

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

Buy any 2 pairs for £75

More Info

116 reviews

Classic Durham Shoe - Tan More Info

Classic Durham Shoe - Tan

£44.95 WAS £100

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

Buy any 2 pairs for £75

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43 reviews

Classic Monk Shoes - Burgundy-Brown More Info

Classic Monk Shoes - Burgundy-Brown

£44.95 WAS £100

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

Buy any 2 pairs for £75

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129 reviews

Classic Deck Shoe - Nubuck More Info

Classic Deck Shoe - Nubuck

£44.95 WAS £100

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

Buy any 2 pairs for £75

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80 reviews

Classic Derby Shoe - Blue More Info

NEW

Classic Derby Shoe - Blue

£44.95 WAS £100

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

Buy any 2 pairs for £75

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11 reviews

Richmond Classics Shoe - Black More Info

Richmond Classics Shoe - Black

£44.95 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.

Buy any 2 pairs for £75

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66 reviews

Classic Sandhurst Shoe - Black More Info

Classic Sandhurst Shoe - Black

£44.95 WAS £100

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

Buy any 2 pairs for £75

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53 reviews

Classic Deck Shoe - Blue/Brown More Info

Classic Deck Shoe - Blue/Brown

£44.95 WAS £100

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

Buy any 2 pairs for £75

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117 reviews

Classic Deck Shoe - Blue/Brown/White More Info

Classic Deck Shoe - Blue/Brown/White

£44.95 WAS £100

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

Buy any 2 pairs for £75

More Info

87 reviews

Classic Claridge Shoe - Black More Info

Classic Claridge Shoe - Black

£44.95 WAS £100

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

Buy any 2 pairs for £75

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32 reviews

Classic Leather Trainer More Info

Classic Leather Trainer

£44.95 WAS £100

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

Buy any 2 pairs for £75

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43 reviews

Classic Monk Shoes - Suede More Info

Classic Monk Shoes - Suede

£44.95 WAS £100

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

Buy any 2 pairs for £75

More Info

37 reviews

Classic Camden Shoe More Info

Classic Camden Shoe

£44.95 WAS £100

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

Buy any 2 pairs for £75

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16 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.