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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

(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

(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

(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

(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

(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

(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

(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

(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

(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

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

(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

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

(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

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

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

Sale Prestige Derby Shoe - Tan

Prestige Derby Shoe - Tan

(15)

Was $159.00 $45.00

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

(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

(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

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

(19)

Was $149.00 $50.00

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

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

(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

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