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    All Men's Shoes

    Discover handmade men's shoes at incredible prices, here at Samuel Windsor. Made from the finest leather and suede, our high quality men's shoes are available in a wide choice of styles and colors. Need some formal shoes? Our smart leather Oxfords take you everywhere from the office to black tie events. Something more sturdy? Check out our prestige men's boots with non-slip rubber soles for rugged, hardwearing comfort.

    Black Shoes Boat Shoes Boots Brogues Brown Shoes Chelsea Boots Chukka Boots Classic Shoes Crepe Sole Boots Derby Shoes Formal Shoes Leather Slippers Lightweight Shoes Loafers Monk Shoes Oxblood Shoes Oxford Shoes Prestige Shoes Sandals Sneakers Tan Shoes Read More
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    New Outdoor Mule - Honey

    Outdoor Mule - Honey

    (0)

    $49.00

    New Outdoor Mule - Navy Nubuck

    Outdoor Mule - Navy Nubuck

    (0)

    $49.00

    New Outdoor Mule - Natural

    Outdoor Mule - Natural

    (0)

    $49.00

    New Leather Soled Sandal - Natural

    Leather Soled Sandal - Natural

    (0)

    $49.00

    New Leather Soled Sandal - Black

    Leather Soled Sandal - Black

    (0)

    $49.00

    New Leather Soled Sandal - Tan

    Leather Soled Sandal - Tan

    (0)

    $49.00

    New Strapless Sandal - Natural

    Strapless Sandal - Natural

    (0)

    $49.00

    Prestige Tweed Brogue - Exmoor

    Prestige Tweed Brogue - Exmoor

    (5)

    Was $189.00 $79.00

    Prestige Chiltern Boot – Dark Brown Waxed Suede

    Prestige Chiltern Boot – Dark Brown Waxed Suede

    (1)

    Was $159.00 $79.00

    Prestige Tweed Brogue Boot – Dartmoor

    Prestige Tweed Brogue Boot – Dartmoor

    (0)

    Was $189.00 $85.00

    Suede Moccasin – Dartmoor

    Suede Moccasin – Dartmoor

    (2)

    Was $85.00 $60.00

    Suede Moccasin – Exmoor

    Suede Moccasin – Exmoor

    (2)

    Was $85.00 $49.00

    Outdoor Mule – Burgundy

    Outdoor Mule – Burgundy

    (8)

    Was $85.00 $49.00

    Prestige Suede Sneakers - Tan

    Prestige Suede Sneakers - Tan

    (8)

    Was $149.00 $70.00

    Prestige Suede Sneakers - Gray

    Prestige Suede Sneakers - Gray

    (5)

    Was $149.00 $70.00

    Prestige Suede Sneakers - Navy

    Prestige Suede Sneakers - Navy

    (8)

    Was $149.00 $70.00

    Prestige Crepe Sole Chelsea Boots - Tan

    Prestige Crepe Sole Chelsea Boots - Tan

    (4)

    Was $159.00 $75.00

    Prestige Crepe Sole Chelsea Boots - Navy

    Prestige Crepe Sole Chelsea Boots - Navy

    (0)

    Was $159.00 $75.00

    Prestige Crepe Sole Desert Boots - Tan

    Prestige Crepe Sole Desert Boots - Tan

    (3)

    Was $159.00 $89.00

    Prestige Crepe Sole Desert Boots - Navy

    Prestige Crepe Sole Desert Boots - Navy

    (4)

    Was $159.00 $75.00

    Prestige Desert Boots - Gray

    Prestige Desert Boots - Gray

    (2)

    Was $159.00 $89.00

    Prestige Lightweight Derby - Navy Suede

    Prestige Lightweight Derby - Navy Suede

    (39)

    Was $149.00 $85.00

    Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (39)

    Was $149.00 $85.00

    Prestige Lightweight Derby - Tobacco

    Prestige Lightweight Derby - Tobacco

    (41)

    Was $149.00 $85.00

    Any 2 pairs for $120

    Prestige Boat Shoe - Gray

    Prestige Boat Shoe - Gray

    (406)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Penny Loafer - Black

    Prestige Penny Loafer - Black

    (320)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Boat Shoe - Tan

    Prestige Boat Shoe - Tan

    (406)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Boat Shoe - Navy

    Prestige Boat Shoe - Navy

    (352)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Penny Loafer - Tan

    Prestige Penny Loafer - Tan

    (263)

    Was $149.00 $65.00

    Sale

    Any 2 pairs for $120

    Prestige Boat Shoe - Dark Olive

    Prestige Boat Shoe - Dark Olive

    (352)

    Was $149.00 $75.00

    Prestige Tasselled Loafer - Sand

    Prestige Tasselled Loafer - Sand

    (31)

    Was $149.00 $50.00

    Sale Classic Lightweight Brogue - Navy

    Classic Lightweight Brogue - Navy

    (43)

    Was $135.00 $69.00 $65.00 Save $4.00

    Any 2 for $100

    Classic Boat Shoe - Blue

    Classic Boat Shoe - Blue

    (43)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Boat Shoe - Tobacco

    Classic Boat Shoe - Tobacco

    (45)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Boat Shoe - Navy/Brown

    Classic Boat Shoe - Navy/Brown

    (130)

    Was $135.00 $55.00

    Sale Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (39)

    Was $149.00 $45.00

    Sale

    Any 2 for $100

    Classic Moccasin

    Classic Moccasin

    (119)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Classic Leather Driving Shoe

    Classic Leather Driving Shoe

    (86)

    Was $135.00 $40.00

    Sale Prestige Driving Shoe - Navy/Brown

    Prestige Driving Shoe - Navy/Brown

    (46)

    Was $149.00 $45.00

    Sale

    Any 2 for $100

    Classic Suede Driving Shoe

    Classic Suede Driving Shoe

    (110)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Penny Loafer - Suede - Black

    Prestige Penny Loafer - Suede - Black

    (29)

    Was $159.00 $45.00

    Any 2 for $100

    Classic Derby Shoe - Suede

    Classic Derby Shoe - Suede

    (10)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Derby Shoe - Black Suede

    Classic Derby Shoe - Black Suede

    (17)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Derby Shoe - Black

    Classic Derby Shoe - Black

    (53)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Chichester Shoe - Oxblood

    Classic Chichester Shoe - Oxblood

    (162)

    Was $135.00 $55.00

    Prestige Chelsea Boot - Rubber Sole - Black

    Prestige Chelsea Boot - Rubber Sole - Black

    (30)

    Was $189.00 $79.00

    Prestige Davington Brogue - Tan

    Prestige Davington Brogue - Tan

    (27)

    Was $159.00 $75.00

    Sale Prestige Belgravia Boot - Black

    Prestige Belgravia Boot - Black

    (225)

    Was $159.00 $50.00

    Sale Prestige Chukka Boot - Black

    Prestige Chukka Boot - Black

    (21)

    Was $189.00 $85.00 $72.50 Save $12.50

    Sale Prestige Chukka Boot - Suede

    Prestige Chukka Boot - Suede

    (16)

    Was $189.00 $85.00 $72.50 Save $12.50

    Prestige Chiltern Boot - Brown

    Prestige Chiltern Boot - Brown

    (46)

    Was $159.00 $79.00

    Prestige Chiltern Boot - Nubuck

    Prestige Chiltern Boot - Nubuck

    (13)

    Was $159.00 $79.00

    Sale Prestige Chukka Boots - Tan

    Prestige Chukka Boots - Tan

    (33)

    Was $189.00 $85.00 $80.00 Save $5.00

    Sale Prestige Davington Brogue - Black

    Prestige Davington Brogue - Black

    (22)

    Was $159.00 $85.00 $72.50 Save $12.50

    Prestige Whitworth Brogue - Tan

    Prestige Whitworth Brogue - Tan

    (187)

    Was $159.00 $75.00

    Sale Classic Slip-On Boat Shoe - Navy/Brown

    Classic Slip-On Boat Shoe - Navy/Brown

    (431)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Classic Slip-On Boat Shoe - Camel

    Classic Slip-On Boat Shoe - Camel

    (431)

    Was $135.00 $69.00 $65.00 Save $4.00

    Prestige Slip-On Boat Shoe - Brown

    Prestige Slip-On Boat Shoe - Brown

    (19)

    Was $149.00 $50.00

    Sale

    Any 2 for $100

    Classic Cheltenham Brogue In Suede - Mid Brown

    Classic Cheltenham Brogue In Suede - Mid Brown

    (69)

    Was $135.00 $69.00 $65.00 Save $4.00

    Any 2 for $100

    Classic Chichester Shoe - Black

    Classic Chichester Shoe - Black

    (162)

    Was $135.00 $55.00

    Sale Classic Oxford Shoe - Tan

    Classic Oxford Shoe - Tan

    (400)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Bartlett Brogue In Suede - Mid Brown

    Prestige Bartlett Brogue In Suede - Mid Brown

    (38)

    Was $149.00 $45.00

    Sale Prestige Suede Chelsea Boot - Black

    Prestige Suede Chelsea Boot - Black

    (27)

    Was $189.00 $55.00

    Sale Prestige Suede Chelsea Boot - Brown

    Prestige Suede Chelsea Boot - Brown

    (40)

    Was $189.00 $50.00

    Sale Prestige Monk Boot - Black

    Prestige Monk Boot - Black

    (34)

    Was $159.00 $85.00 $72.50 Save $12.50

    Sale Prestige Country Boot - Black

    Prestige Country Boot - Black

    (104)

    Was $189.00 $85.00 $80.00 Save $5.00

    Any 2 for $100

    Classic Monk Shoe - Black

    Classic Monk Shoe - Black

    (2438)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Monk Shoe - Brown

    Classic Monk Shoe - Brown

    (1667)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Penny Loafer Shoe - Black

    Classic Penny Loafer Shoe - Black

    (4123)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Penny Loafer - Brown

    Classic Penny Loafer - Brown

    (2125)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Oxford Shoe - Brown

    Classic Oxford Shoe - Brown

    (2525)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Oxblood Cheltenham Brogue

    Classic Oxblood Cheltenham Brogue

    (313)

    Was $135.00 $55.00

    Sale

    Any 2 for $100

    Classic Suede Oxford Shoe

    Classic Suede Oxford Shoe

    (79)

    Was $135.00 $69.00 $65.00 Save $4.00

    Any 2 for $100

    Classic Oxford Shoe - Oxblood

    Classic Oxford Shoe - Oxblood

    (360)

    Was $135.00 $55.00

    Sale

    Any 2 for $100

    Classic Cheltenham Brogue in Suede

    Classic Cheltenham Brogue in Suede

    (150)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Classic Tan Cheltenham Brogue

    Classic Tan Cheltenham Brogue

    (178)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 for $100

    Classic Sandhurst Shoe

    Classic Sandhurst Shoe

    (1332)

    Was $135.00 $69.00 $65.00 Save $4.00

    Any 2 for $100

    Classic Penny Loafer - Black Suede

    Classic Penny Loafer - Black Suede

    (79)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Monk Brogue - Black

    Classic Monk Brogue - Black

    (283)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Slip-On Boat Shoe

    Classic Slip-On Boat Shoe

    (431)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Semi-Brogue - Black

    Classic Semi-Brogue - Black

    (4135)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Boat Shoe

    Classic Boat Shoe

    (750)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Penny Loafer - Dark Brown Suede

    Classic Penny Loafer - Dark Brown Suede

    (384)

    Was $135.00 $55.00

    Sale

    Any 2 for $100

    Classic Penny Loafer - Brown Suede

    Classic Penny Loafer - Brown Suede

    (958)

    Was $135.00 $75.00 $65.00 Save $10.00

    Any 2 for $100

    Classic Oxford Shoe - Black

    Classic Oxford Shoe - Black

    (8333)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Quarter-Brogue - Black

    Classic Quarter-Brogue - Black

    (1786)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Cheltenham Brogue - Black

    Classic Cheltenham Brogue - Black

    (3246)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Kempton Shoe - Black

    Classic Kempton Shoe - Black

    (2090)

    Was $135.00 $55.00

    Any 2 for $100

    Classic Kempton Shoe

    Classic Kempton Shoe

    (2652)

    Was $135.00 $55.00

    Any 2 pairs for $120

    Prestige Tasselled Loafer - Black

    Prestige Tasselled Loafer - Black

    (605)

    Was $149.00 $65.00

    Prestige Oxford Shoe - Rubber Sole - Black

    Prestige Oxford Shoe - Rubber Sole - Black

    (2329)

    Was $159.00 $75.00

    Sale Prestige Brogue - Rubber Sole

    Prestige Brogue - Rubber Sole

    (767)

    Was $159.00 $50.00

    Any 2 pairs for $120

    Prestige Oxford Dress Shoe - Black

    Prestige Oxford Dress Shoe - Black

    (133)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Dress Shoe - Black

    Prestige Dress Shoe - Black

    (246)

    Was $149.00 $65.00

    Sale Prestige Whitworth Brogue - Black

    Prestige Whitworth Brogue - Black

    (86)

    Was $159.00 $85.00 $72.50 Save $12.50

    Prestige Whitworth Brogue

    Prestige Whitworth Brogue

    (187)

    Was $159.00 $75.00

    Prestige Bartlett Brogue - Tan

    Prestige Bartlett Brogue - Tan

    (143)

    Was $159.00 $75.00

    Prestige Brogue - Black

    Prestige Brogue - Black

    (169)

    Was $159.00 $75.00

    Prestige Split Brogue - Brown

    Prestige Split Brogue - Brown

    (185)

    Was $159.00 $75.00

    Sale Prestige Oxford Shoe - Rubber Sole

    Prestige Oxford Shoe - Rubber Sole

    (47)

    Was $179.00 $45.00

    Prestige Oxford - Black

    Prestige Oxford - Black

    (229)

    Was $159.00 $75.00

    Sale Prestige Country Brogue - Rubber Sole

    Prestige Country Brogue - Rubber Sole

    (325)

    Was $179.00 $85.00 $72.50 Save $12.50

    Any 2 pairs for $120

    Prestige Leather Lace-Up Boat Shoe

    Prestige Leather Lace-Up Boat Shoe

    (406)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Boat Shoe

    Prestige Boat Shoe

    (312)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Lace-Up Boat Shoe

    Prestige Lace-Up Boat Shoe

    (241)

    Was $149.00 $65.00

    Sale Prestige Cumbria Boot

    Prestige Cumbria Boot

    (191)

    Was $159.00 $85.00 $80.00 Save $5.00

    Any 2 pairs for $120

    Prestige Twin Monk Shoe - Oxblood

    Prestige Twin Monk Shoe - Oxblood

    (144)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Twin Monk - Black

    Prestige Twin Monk - Black

    (187)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Slip-On Boat Shoe - Brown

    Prestige Slip-On Boat Shoe - Brown

    (352)

    Was $149.00 $65.00

    Any 2 pairs for $120

    Prestige Slip-On Boat Shoe

    Prestige Slip-On Boat Shoe

    (340)

    Was $149.00 $65.00

    Sale Prestige Penny Loafer - Black

    Prestige Penny Loafer - Black

    (320)

    Was $149.00 $50.00

    Sale Prestige Penny Loafer

    Prestige Penny Loafer

    (263)

    Was $149.00 $50.00

    Sale Prestige Semi-Brogue

    Prestige Semi-Brogue

    (591)

    Was $149.00 $50.00

    Any 2 pairs for $120

    Prestige Oxford Shoe - Black

    Prestige Oxford Shoe - Black

    (807)

    Was $149.00 $65.00

    Prestige Chelsea Boot - Black

    Prestige Chelsea Boot - Black

    (1486)

    Was $159.00 $79.00

    Prestige Chelsea Boot

    Prestige Chelsea Boot

    (346)

    Was $159.00 $79.00

    Prestige Suede Chelsea Boot

    Prestige Suede Chelsea Boot

    (764)

    Was $159.00 $79.00

    Sale Prestige Semi-Brogue - Black

    Prestige Semi-Brogue - Black

    (868)

    Was $149.00 $50.00

    Sale Prestige Belgravia Shoe

    Prestige Belgravia Shoe

    (225)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Kensington Boot - Rubber Sole - Black

    Prestige Kensington Boot - Rubber Sole - Black

    (322)

    Was $189.00 $55.00

    Sale Prestige Country Boot - Rubber Sole - Tan

    Prestige Country Boot - Rubber Sole - Tan

    (273)

    Was $189.00 $85.00 $80.00 Save $5.00

    Grecian Slipper - Navy

    Grecian Slipper - Navy

    (86)

    Was $85.00 $49.00

    Grecian Slipper - Black

    Grecian Slipper - Black

    (207)

    Was $85.00 $49.00

    Grecian Slipper - Brown

    Grecian Slipper - Brown

    (204)

    Was $85.00 $49.00

    Albert Slipper - Black

    Albert Slipper - Black

    (317)

    Was $85.00 $49.00

    Mule - Black

    Mule - Black

    (240)

    Was $85.00 $49.00

    Albert Slipper - Brown

    Albert Slipper - Brown

    (274)

    Was $85.00 $49.00

    Mule - Brown

    Mule - Brown

    (122)

    Was $85.00 $49.00

    Albert Slipper - Oxblood

    Albert Slipper - Oxblood

    (200)

    Was $85.00 $49.00

    Handmade Leather Sandal - Single Cross - Tan

    Handmade Leather Sandal - Single Cross - Tan

    (51)

    Was $89.00 $49.00

    Handmade Leather Sandal - Touch Fasten - Brown

    Handmade Leather Sandal - Touch Fasten - Brown

    (94)

    Was $89.00 $49.00

    Fisherman's Sandals

    Fisherman's Sandals

    (119)

    Was $89.00 $49.00

    Churchill Fleece Lined Outdoor Mule - Brown

    Churchill Fleece Lined Outdoor Mule - Brown

    (233)

    Was $85.00 $49.00

    Outdoor Mule - Black

    Outdoor Mule - Black

    (652)

    Was $85.00 $49.00

    Outdoor Mule - Brown

    Outdoor Mule - Brown

    (1332)

    Was $85.00 $49.00

    Samuel Windsor

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