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92%
112,960

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Most Popular

  1. Classic Oxford Shoe
    £47.95

  2. Classic Cheltenham Brogue
    £47.95

  3. Classic Penny Loafer Shoe
    £47.95

  4. Pleated Chino Trousers
    £17.50

  5. Classic Oxford Shoe
    £47.95

  6. Moleskin Jeans
    £20.00

  7. Flat Front Chino
    £17.50

  8. Classic Monk Shoe
    £47.95

  9. Prestige Oxford Shoe
    £64.95

  10. Classic Semi-Brogue
    £47.95

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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94% (163)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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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92% (854)
Classic Semi-Brogue

Classic Semi-Brogue

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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92% (123)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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92% (129)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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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94% (247)
Classic Monk Shoe

Classic Monk Shoe

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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90% (157)
Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Tasselled Loafer - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (68)
Prestige Brogue - Rubber Sole - Black

Prestige Brogue - Rubber Sole - Black

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

Prestige Brogue: Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (75)
Prestige Brogue - Rubber Sole

Prestige Brogue - Rubber Sole

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

Prestige Brogue: Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (86)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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90% (25)
Prestige Kensington Boot - Rubber Sole

Prestige Kensington Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Kensington Boot - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (57)
Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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90% (71)
Prestige Tasselled Suede Loafer

Prestige Tasselled Suede Loafer

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Tasselled Loafer - Blue Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (45)
Prestige Country Brogue - Rubber Sole

Prestige Country Brogue - Rubber Sole

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Country Brogue - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (49)
Prestige Lightweight Derby Shoe

Prestige Lightweight Derby Shoe

£64.95

Typical High Street Price: £126.33

ANY 2 PAIRS £99

Prestige Lightweight Derby Shoe - Sand Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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no reviews
Classic Durham Shoe

Classic Durham Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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90% (60)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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86% (78)
Classic Deck Shoe

Classic Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY 2 PAIRS £80

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

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90% (150)
Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Penny Loafer - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (81)
Prestige Penny Loafer

Prestige Penny Loafer

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Penny Loafer - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (73)
Prestige Monk Shoe - Rubber Sole - Black

Prestige Monk Shoe - Rubber Sole - Black

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

Prestige Monk Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (31)
Prestige Gibson Shoe - Rubber Sole

Prestige Gibson Shoe - Rubber Sole

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

Prestige Gibson Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (51)
Prestige Kensington Boot - Rubber Sole - Black

Prestige Kensington Boot - Rubber Sole - Black

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Kensington Boot - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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86% (53)
Classic Deck Shoe

Classic Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY 2 PAIRS £80

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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no reviews
Prestige Derby Shoe

Prestige Derby Shoe

£64.95

Typical High Street Price: £126.33

ANY 2 PAIRS £99

Prestige Derby Shoe - Navy Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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100% (1)
Classic Oxford Shoe

Classic Oxford Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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94% (111)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£64.95

Typical High Street Price: £111.00

ANY 2 PAIRS £99

Prestige Leather Slip-On Boat Shoe - made with the finest Italian leather uppers or a luxury finish and unbeatable comfort and durability.

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90% (129)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£64.95

Typical High Street Price: £111.00

ANY 2 PAIRS £99

Our Prestige Slip-on Boat Shoes with contrasting colours is the epitome of casual sophistication. Visit us now for great offers on leather deck shoes.

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88% (139)
Classic Lace-Up Deck Shoe

Classic Lace-Up Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY 2 PAIRS £80

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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90% (58)
Prestige Cumbria Boot

Prestige Cumbria Boot

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Prestige Cumbria Boot - Mid Brown, a lace-up shoe with an exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

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92% (57)
Prestige Lace-Up Deck Shoe

Prestige Lace-Up Deck Shoe

£64.95

Typical High Street Price: £111.00

ANY 2 PAIRS £99

Prestige Leather Lace-Up Boat Shoe - exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

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90% (148)
Prestige Lace-Up Deck Shoe

Prestige Lace-Up Deck Shoe

£64.95

Typical High Street Price: £111.00

ANY 2 PAIRS £99

Our Prestige Lace-Up Boat Shoes with contrasting colours is the epitome of casual sophistication. Visit us now for great offers on leather deck shoes.

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94% (63)
Prestige Lightweight Brogue

Prestige Lightweight Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Lightweight Brogue - Tobacco, a brogue shoe with an exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

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no reviews
Prestige Leather/Canvas Brogue

SALE

Prestige Leather/Canvas Brogue

£25.00

Typical High Street Price: £129.50

Save £104.50

Leather and canvas brogues from our Prestige range are the pinnacle of versatility. Choose from a range of colours at Samuel Windsor online.

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90% (47)
Prestige Leather/Canvas Brogue

SALE

Prestige Leather/Canvas Brogue

£25.00

Typical High Street Price: £129.50

Save £104.50

Prestige Leather/Canvas Brogue from our Prestige range are the pinnacle of versatility.

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96% (81)
Prestige Deck Shoe

Prestige Deck Shoe

£64.95

Typical High Street Price: £111.00

ANY 2 PAIRS £99

These Prestige deck shoes are supremely comfortable, fabulously affordable and crafted using Italian leather. Visit now for great offers.

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90% (76)
Prestige Dress Shoe

Prestige Dress Shoe

£64.95

Typical High Street Price: £92.25

ANY 2 PAIRS £99

Shopping for men's dress shoes? Add the finishing touch to your formal outfit with Samuel Windsor prestige dress shoes, made from fine Italian leather.

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96% (78)
Prestige Country Boot - Rubber Sole

Prestige Country Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Country Boot - Antique Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (55)
Prestige Country Boot - Rubber Sole

Prestige Country Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Country Boot, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (58)
Classic Oxford Shoe - Cigar

Classic Oxford Shoe - Cigar

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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92% (62)
Classic Semi-Brogue

Classic Semi-Brogue

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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86% (68)
Classic Quarter-Brogue

Classic Quarter-Brogue

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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92% (41)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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90% (48)
Prestige Oxford Shoe

Prestige Oxford Shoe

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Featuring a classic Oxford shoe design, these Goodyear Welted men’s shoes offer all the luxury you could ask for.

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86% (29)
Prestige Belgravia Shoe

Prestige Belgravia Shoe

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

These nubuck men’s boots are a great addition to any gent’s wardrobe.

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94% (58)
Prestige Chelsea Boot

Prestige Chelsea Boot

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boot, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (88)
Prestige Tasselled Loafer

Prestige Tasselled Loafer

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Tasselled Loafer - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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80% (22)
Classic Driving Shoe

Classic Driving Shoe

£47.95

Typical High Street Price: £80.00

ANY 2 PAIRS £80

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

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100% (1)
Classic Moccasin

Classic Moccasin

£47.95

Typical High Street Price: £80.00

ANY 2 PAIRS £80

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

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100% (2)
Prestige Brogue

Prestige Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Brown Brogues, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (35)
Prestige Oxford

Prestige Oxford

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Oxford Shoe, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (74)
Prestige Split Brogue

Prestige Split Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Make an entrance with Samuel Windsor Prestige Split Brogues. Its two-tone style and punch detailing make for an outstanding finish.

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90% (70)
Prestige Twin Monk

Prestige Twin Monk

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Twin Monk, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (59)
Prestige Brogue

Prestige Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Black Brogues, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (78)
Prestige Lightweight Brogue

Prestige Lightweight Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Suede Brogues, online from Samuel Windsor. Visit us now for exceptional quality at outstanding prices.

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80% (1)
Classic Deck Shoe

Classic Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY 2 PAIRS £80

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

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80% (2)
Classic Durham Shoe

Classic Durham Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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

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88% (43)
Classic Monk Brogue

Classic Monk Brogue

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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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90% (48)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

Buy classic suede brogues from Samuel Windsor. Our handmade suede brogues offer a casual variation of this classic brogue design.

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94% (29)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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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94% (39)
Prestige Oxford Dress Shoe

Prestige Oxford Dress Shoe

£64.95

Typical High Street Price: £92.25

ANY 2 PAIRS £99

Shopping for mens dress shoes? Add the finishing touch to your formal outfit with prestige Oxford dress shoes, from Samuel Windsor online.

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90% (17)
Prestige Chelsea Brogue Boot - Rubber Sole

Prestige Chelsea Brogue Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Brogue Boot - Rubber Sole is made by hand using Goodyear Welted construction.

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84% (40)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Buy Prestige Chukka Boots from Samuel Windsor. Rubber soles and Italian leather suede make this classic boot the perfect choice for a smart casual outfit.

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94% (22)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Buy Burgundy Chukka Boots from Samuel Windsor. Rubber soles and Italian leather suede make this classic boot the perfect choice for a smart casual outfit.

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90% (11)
Prestige Split Brogue

Prestige Split Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Split Brogue, online from Samuel Windsor. Tailored quality at outstanding prices.

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80% (10)
Prestige Split Brogue Oxblood

Prestige Split Brogue Oxblood

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Make an entrance with Oxblood Prestige Split Brogues from Samuel Windsor. Its two-tone style and punch detailing make for an outstanding finish.

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96% (22)
Prestige Cheltenham Brogue

Prestige Cheltenham Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Buy premium brogues online from Samuel Windsor. Stand out from the crowd in our premium suede brogues, handmade to provide style, elegance and comfort.

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88% (7)
Prestige Balham Boot - Brown

NEW

Prestige Balham Boot - Brown

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Prestige Balham Boot - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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80% (1)
Prestige Balham Boot - Black

NEW

Prestige Balham Boot - Black

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Prestige Balham Boot - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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no reviews
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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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90% (417)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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90% (195)
Classic Oxford Shoe

Classic Oxford Shoe

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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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94% (289)
Classic City Shoe - Black

Classic City Shoe - Black

£47.95

Typical High Street Price: £126.33

ANY 2 PAIRS £80

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

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86% (104)
Prestige Oxford Shoe - Rubber Sole - Black

Prestige Oxford Shoe - Rubber Sole - Black

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

Black Oxford Shoes Rubber Sole, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (117)
Classic Richmond Shoe - Black

Classic Richmond Shoe - Black

£47.95

Typical High Street Price: £126.33

ANY 2 PAIRS £80

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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88% (71)
Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

£47.95

Typical High Street Price: £129.50

ANY 2 PAIRS £80

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.

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92% (485)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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92% (175)
Classic Kempton Shoe

Classic Kempton Shoe

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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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94% (339)
Nubuck Trainer

SALE

Nubuck Trainer

£27.50

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

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88% (61)
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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86% (53)
Prestige Gibson Shoe

Prestige Gibson Shoe

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

These Goodyear Welted, Prestige Gibson shoes, featuring Italian grained leather uppers, as well as a practical rubber sole, they have country styling, and are ideal as a more subtle choice of quality men’s shoe.

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92% (30)
Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Oxford Black Shoe - Italian Leather Upper, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (76)
Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boots: Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (161)
Prestige Suede Chelsea Boot

Prestige Suede Chelsea Boot

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boots: Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (80)
Prestige Semi-Brogue - Black

Prestige Semi-Brogue - Black

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Semi-Brogue - Black - Italian Leather Upper, online from Samuel Windsor. Tailored quality at outstanding prices.

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86% (36)
Prestige Semi-Brogue

Prestige Semi-Brogue

£64.95

Typical High Street Price: £129.50

ANY 2 PAIRS £99

Prestige Semi-Brogue - Tan - Italian Leather Upper, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (36)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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90% (105)