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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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    Outdoor Mule - Brown

    Outdoor Mule - Brown

    (1318)

    Was $85.00 $55.00

    Sale

    Any 2 for $120

    Classic Oxford Shoe - Black

    Classic Oxford Shoe - Black

    (8329)

    Was $135.00 $69.00 $65.00 Save $4.00

    Outdoor Mule - Black

    Outdoor Mule - Black

    (640)

    Was $85.00 $55.00

    Sale

    Any 2 for $120

    Classic Oxford Shoe - Brown

    Classic Oxford Shoe - Brown

    (2525)

    Was $135.00 $69.00 $65.00 Save $4.00

    Mule - Black

    Mule - Black

    (230)

    Was $85.00 $55.00

    Sale

    Any 2 for $120

    Classic Oxford Shoe - Oxblood

    Classic Oxford Shoe - Oxblood

    (351)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 for $120

    Classic Chichester Shoe - Black

    Classic Chichester Shoe - Black

    (155)

    Was $135.00 $69.00 $65.00 Save $4.00

    Albert Slipper - Oxblood

    Albert Slipper - Oxblood

    (189)

    Was $85.00 $55.00

    Sale

    Any 2 for $120

    Classic Oxblood Cheltenham Brogue

    Classic Oxblood Cheltenham Brogue

    (313)

    Was $135.00 $69.00 $65.00 Save $4.00

    Albert Slipper - Black

    Albert Slipper - Black

    (312)

    Was $85.00 $55.00

    Sale

    Any 2 for $120

    Classic Kempton Shoe

    Classic Kempton Shoe

    (2653)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale

    Any 2 for $120

    Classic Penny Loafer Shoe - Black

    Classic Penny Loafer Shoe - Black

    (4123)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale

    Any 2 for $120

    Classic Cheltenham Brogue - Black

    Classic Cheltenham Brogue - Black

    (3243)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 for $120

    Classic Chichester Shoe - Oxblood

    Classic Chichester Shoe - Oxblood

    (155)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 pairs for $130

    Prestige Twin Monk Shoe - Oxblood

    Prestige Twin Monk Shoe - Oxblood

    (143)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Kempton Shoe - Black

    Classic Kempton Shoe - Black

    (2089)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale

    Any 2 for $120

    Classic Penny Loafer - Brown

    Classic Penny Loafer - Brown

    (2125)

    Was $135.00 $75.00 $65.00 Save $10.00

    Mule - Brown

    Mule - Brown

    (120)

    Was $85.00 $55.00

    Sale

    Any 2 for $120

    Classic Derby Shoe - Black

    Classic Derby Shoe - Black

    (48)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale Prestige Whitworth Brogue

    Prestige Whitworth Brogue

    (184)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 pairs for $130

    Prestige Boat Shoe

    Prestige Boat Shoe

    (307)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 pairs for $130

    Prestige Tasselled Loafer - Black

    Prestige Tasselled Loafer - Black

    (605)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Monk Shoe - Black

    Classic Monk Shoe - Black

    (2433)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Country Boot - Black

    Prestige Country Boot - Black

    (101)

    Was $189.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 for $120

    Classic Monk Shoe - Brown

    Classic Monk Shoe - Brown

    (1667)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Split Brogue - Brown

    Prestige Split Brogue - Brown

    (184)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 pairs for $130

    Prestige Dress Shoe - Black

    Prestige Dress Shoe - Black

    (244)

    Was $149.00 $75.00 $72.50 Save $2.50

    Fisherman's Sandals

    Fisherman's Sandals

    (119)

    Was $89.00 $55.00

    Sale

    Any 2 for $120

    Classic Monk Brogue - Black

    Classic Monk Brogue - Black

    (281)

    Was $135.00 $69.00 $65.00 Save $4.00

    Grecian Slipper - Navy

    Grecian Slipper - Navy

    (86)

    Was $85.00 $55.00

    Sale

    Any 2 pairs for $130

    Prestige Twin Monk - Black

    Prestige Twin Monk - Black

    (184)

    Was $149.00 $75.00 $72.50 Save $2.50

    Grecian Slipper - Black

    Grecian Slipper - Black

    (204)

    Was $85.00 $55.00

    Sale

    Any 2 for $120

    Classic Derby Shoe - Black Suede

    Classic Derby Shoe - Black Suede

    (16)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale Prestige Chelsea Boot - Black

    Prestige Chelsea Boot - Black

    (1483)

    Was $159.00 $85.00 $80.00 Save $5.00

    Handmade Leather Sandal - Single Cross - Tan

    Handmade Leather Sandal - Single Cross - Tan

    (51)

    Was $89.00 $55.00

    Sale

    Any 2 for $120

    Classic Oxford Shoe - Tan

    Classic Oxford Shoe - Tan

    (400)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 for $120

    Classic Sandhurst Shoe

    Classic Sandhurst Shoe

    (1332)

    Was $135.00 $69.00 $65.00 Save $4.00

    Grecian Slipper - Brown

    Grecian Slipper - Brown

    (201)

    Was $85.00 $55.00

    Sale

    Any 2 for $120

    Classic Boat Shoe - Navy/Brown

    Classic Boat Shoe - Navy/Brown

    (128)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 for $120

    Classic Penny Loafer - Black Suede

    Classic Penny Loafer - Black Suede

    (79)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale

    Any 2 for $120

    Classic Boat Shoe

    Classic Boat Shoe

    (751)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Oxford - Black

    Prestige Oxford - Black

    (228)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 for $120

    Classic Quarter-Brogue - Black

    Classic Quarter-Brogue - Black

    (1785)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 pairs for $130

    Prestige Slip-On Boat Shoe - Brown

    Prestige Slip-On Boat Shoe - Brown

    (350)

    Was $149.00 $75.00 $72.50 Save $2.50

    Churchill Fleece Lined Outdoor Mule - Brown

    Churchill Fleece Lined Outdoor Mule - Brown

    (228)

    Was $85.00 $55.00

    Sale

    Any 2 pairs for $130

    Prestige Leather Lace-Up Boat Shoe

    Prestige Leather Lace-Up Boat Shoe

    (404)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Slip-On Boat Shoe

    Classic Slip-On Boat Shoe

    (428)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 pairs for $130

    Prestige Oxford Shoe - Black

    Prestige Oxford Shoe - Black

    (805)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Penny Loafer - Brown Suede

    Classic Penny Loafer - Brown Suede

    (958)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale

    Any 2 pairs for $130

    Prestige Penny Loafer - Tan

    Prestige Penny Loafer - Tan

    (261)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale Prestige Oxford Shoe - Rubber Sole - Black

    Prestige Oxford Shoe - Rubber Sole - Black

    (2328)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 pairs for $130

    Prestige Slip-On Boat Shoe

    Prestige Slip-On Boat Shoe

    (339)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale Prestige Chukka Boots - Tan

    Prestige Chukka Boots - Tan

    (31)

    Was $189.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 for $120

    Classic Cheltenham Brogue In Suede - Mid Brown

    Classic Cheltenham Brogue In Suede - Mid Brown

    (68)

    Was $135.00 $69.00 $65.00 Save $4.00

    Albert Slipper - Brown

    Albert Slipper - Brown

    (273)

    Was $85.00 $55.00

    Sale

    Any 2 pairs for $130

    Prestige Suede Sneakers - Gray

    Prestige Suede Sneakers - Gray

    (5)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Suede Oxford Shoe

    Classic Suede Oxford Shoe

    (79)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 for $120

    Classic Semi-Brogue - Black

    Classic Semi-Brogue - Black

    (4134)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Penny Loafer

    Prestige Penny Loafer

    (261)

    Was $149.00 $50.00

    Sale

    Any 2 for $120

    Classic Penny Loafer - Dark Brown Suede

    Classic Penny Loafer - Dark Brown Suede

    (384)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale

    Any 2 pairs for $130

    Prestige Suede Sneakers - Navy

    Prestige Suede Sneakers - Navy

    (7)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale Prestige Country Boot - Rubber Sole - Tan

    Prestige Country Boot - Rubber Sole - Tan

    (272)

    Was $189.00 $85.00 $80.00 Save $5.00

    Sale Prestige Chelsea Boot

    Prestige Chelsea Boot

    (345)

    Was $159.00 $85.00 $80.00 Save $5.00

    Handmade Leather Sandal - Touch Fasten - Brown

    Handmade Leather Sandal - Touch Fasten - Brown

    (96)

    Was $89.00 $55.00

    Sale

    Any 2 pairs for $130

    Prestige Oxford Dress Shoe - Black

    Prestige Oxford Dress Shoe - Black

    (131)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale Prestige Bartlett Brogue - Tan

    Prestige Bartlett Brogue - Tan

    (141)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 pairs for $130

    Prestige Boat Shoe - Gray

    Prestige Boat Shoe - Gray

    (404)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Tan Cheltenham Brogue

    Classic Tan Cheltenham Brogue

    (178)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Penny Loafer - Black

    Prestige Penny Loafer - Black

    (319)

    Was $149.00 $50.00

    Sale

    Any 2 for $120

    Classic Derby Shoe - Suede

    Classic Derby Shoe - Suede

    (9)

    Was $135.00 $75.00 $65.00 Save $10.00

    Sale Prestige Chelsea Boot - Rubber Sole - Black

    Prestige Chelsea Boot - Rubber Sole - Black

    (30)

    Was $189.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 pairs for $130

    Prestige Lace-Up Boat Shoe

    Prestige Lace-Up Boat Shoe

    (241)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 pairs for $130

    Prestige Suede Sneakers - Tan

    Prestige Suede Sneakers - Tan

    (7)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale Prestige Semi-Brogue

    Prestige Semi-Brogue

    (591)

    Was $149.00 $50.00

    Sale Prestige Suede Chelsea Boot - Brown

    Prestige Suede Chelsea Boot - Brown

    (39)

    Was $189.00 $50.00

    Sale Prestige Monk Boot - Black

    Prestige Monk Boot - Black

    (33)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 for $120

    Classic Cheltenham Brogue in Suede

    Classic Cheltenham Brogue in Suede

    (150)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Suede Chelsea Boot

    Prestige Suede Chelsea Boot

    (762)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (38)

    Was $149.00 $45.00

    Sale Classic Leather Driving Shoe

    Classic Leather Driving Shoe

    (85)

    Was $135.00 $40.00

    Prestige Crepe Sole Desert Boots - Tan

    Prestige Crepe Sole Desert Boots - Tan

    (3)

    Was $159.00 $75.00

    Sale Prestige Chiltern Boot - Brown

    Prestige Chiltern Boot - Brown

    (44)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 pairs for $130

    Prestige Boat Shoe - Tan

    Prestige Boat Shoe - Tan

    (404)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale Prestige Oxford Shoe - Rubber Sole

    Prestige Oxford Shoe - Rubber Sole

    (46)

    Was $179.00 $45.00

    Sale Prestige Cumbria Boot

    Prestige Cumbria Boot

    (190)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Brogue - Black

    Prestige Brogue - Black

    (169)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Belgravia Shoe

    Prestige Belgravia Shoe

    (224)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Classic City Shoe - Black

    Classic City Shoe - Black

    (2950)

    Was $135.00 $40.00

    Sale

    Any 2 for $120

    Classic Lightweight Brogue - Navy

    Classic Lightweight Brogue - Navy

    (43)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Chiltern Boot - Nubuck

    Prestige Chiltern Boot - Nubuck

    (13)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Brogue - Rubber Sole

    Prestige Brogue - Rubber Sole

    (767)

    Was $159.00 $50.00

    Sale Prestige Davington Brogue - Black

    Prestige Davington Brogue - Black

    (22)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Davington Brogue - Tan

    Prestige Davington Brogue - Tan

    (26)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 for $120

    Classic Suede Driving Shoe

    Classic Suede Driving Shoe

    (110)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Prestige Penny Loafer Suede - Navy

    Prestige Penny Loafer Suede - Navy

    (95)

    Was $159.00 $45.00

    Sale Prestige Suede Chelsea Boot - Black

    Prestige Suede Chelsea Boot - Black

    (27)

    Was $189.00 $55.00

    Sale Prestige Brogue - Rubber Sole - Black

    Prestige Brogue - Rubber Sole - Black

    (567)

    Was $159.00 $50.00

    Sale

    Any 2 for $120

    Classic Moccasin

    Classic Moccasin

    (119)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale Classic Lightweight Brogue - Sand

    Classic Lightweight Brogue - Sand

    (41)

    Was $135.00 $45.00

    Sale Prestige Semi-Brogue - Black

    Prestige Semi-Brogue - Black

    (868)

    Was $149.00 $50.00

    Sale

    Any 2 pairs for $130

    Prestige Penny Loafer - Black

    Prestige Penny Loafer - Black

    (319)

    Was $149.00 $75.00 $72.50 Save $2.50

    Prestige Crepe Sole Chelsea Boots - Tan

    Prestige Crepe Sole Chelsea Boots - Tan

    (4)

    Was $159.00 $75.00

    Sale Prestige Bartlett Brogue In Suede - Mid Brown

    Prestige Bartlett Brogue In Suede - Mid Brown

    (38)

    Was $149.00 $45.00

    Sale Prestige Kensington Boot - Rubber Sole - Black

    Prestige Kensington Boot - Rubber Sole - Black

    (320)

    Was $189.00 $55.00

    Sale Prestige Derby Shoe - Tan

    Prestige Derby Shoe - Tan

    (15)

    Was $159.00 $45.00

    Prestige Desert Boots - Gray

    Prestige Desert Boots - Gray

    (1)

    Was $159.00 $75.00

    Sale Prestige Whitworth Brogue - Black

    Prestige Whitworth Brogue - Black

    (85)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Driving Shoe - Navy/Brown

    Prestige Driving Shoe - Navy/Brown

    (46)

    Was $149.00 $45.00

    Sale Prestige Penny Loafer - Suede - Black

    Prestige Penny Loafer - Suede - Black

    (28)

    Was $159.00 $45.00

    Sale Prestige Chukka Boot - Suede

    Prestige Chukka Boot - Suede

    (15)

    Was $189.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 pairs for $130

    Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (38)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 pairs for $130

    Prestige Lightweight Derby - Tobacco

    Prestige Lightweight Derby - Tobacco

    (41)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Boat Shoe - Tobacco

    Classic Boat Shoe - Tobacco

    (45)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 pairs for $130

    Prestige Lightweight Derby - Navy Suede

    Prestige Lightweight Derby - Navy Suede

    (38)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Slip-On Boat Shoe - Navy/Brown

    Classic Slip-On Boat Shoe - Navy/Brown

    (428)

    Was $135.00 $69.00 $65.00 Save $4.00

    Prestige Tasselled Loafer - Sand

    Prestige Tasselled Loafer - Sand

    (31)

    Was $149.00 $50.00

    Sale

    Any 2 for $120

    Classic Slip-On Boat Shoe - Camel

    Classic Slip-On Boat Shoe - Camel

    (428)

    Was $135.00 $69.00 $65.00 Save $4.00

    Prestige Whitworth Brogue - Tan

    Prestige Whitworth Brogue - Tan

    (184)

    Was $159.00 $75.00

    Sale

    Any 2 pairs for $130

    Prestige Boat Shoe - Navy

    Prestige Boat Shoe - Navy

    (350)

    Was $149.00 $75.00 $72.50 Save $2.50

    Prestige Crepe Sole Desert Boots - Navy

    Prestige Crepe Sole Desert Boots - Navy

    (3)

    Was $159.00 $75.00

    Sale

    Any 2 for $120

    Classic Boat Shoe - Blue

    Classic Boat Shoe - Blue

    (42)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 pairs for $130

    Prestige Boat Shoe - Dark Olive

    Prestige Boat Shoe - Dark Olive

    (350)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale Prestige Belgravia Boot - Black

    Prestige Belgravia Boot - Black

    (224)

    Was $159.00 $50.00

    Prestige Slip-On Boat Shoe - Brown

    Prestige Slip-On Boat Shoe - Brown

    (19)

    Was $149.00 $50.00

    Prestige Leyton Boot - Burgundy

    Prestige Leyton Boot - Burgundy

    (34)

    Was $159.00 $59.00

    Sale Prestige Chukka Boot - Black

    Prestige Chukka Boot - Black

    (21)

    Was $189.00 $85.00 $80.00 Save $5.00

    Prestige Crepe Sole Chelsea Boots - Navy

    Prestige Crepe Sole Chelsea Boots - Navy

    (0)

    Was $159.00 $75.00

    New Outdoor Mule – Burgundy

    Outdoor Mule – Burgundy

    (5)

    Was $85.00 $60.00

    New Suede Moccasin – Dartmoor

    Suede Moccasin – Dartmoor

    (1)

    Was $85.00 $60.00

    Prestige Suede Chelsea Boot - Navy

    Prestige Suede Chelsea Boot - Navy

    (59)

    Was $159.00 $59.00

    Sale Prestige Tweed Brogue Boot – Dartmoor

    Prestige Tweed Brogue Boot – Dartmoor

    (0)

    Was $189.00 $99.00 $95.00 Save $4.00

    Sale Prestige Tweed Brogue - Exmoor

    Prestige Tweed Brogue - Exmoor

    (2)

    Was $189.00 $89.00 $85.00 Save $4.00

    Sale Prestige Country Brogue - Rubber Sole

    Prestige Country Brogue - Rubber Sole

    (325)

    Was $179.00 $85.00 $80.00 Save $5.00

    New Suede Moccasin – Exmoor

    Suede Moccasin – Exmoor

    (1)

    Was $85.00 $60.00

    Sale Prestige Chiltern Boot – Dark Brown Waxed Suede

    Prestige Chiltern Boot – Dark Brown Waxed Suede

    (0)

    Was $159.00 $85.00 $80.00 Save $5.00

    Samuel Windsor

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