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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
New Outdoor Mule - Natural

Prestige Tweed Brogue - Exmoor

(5)

Was $189.00 $79.00

Suede Moccasin – Dartmoor

(2)

Was $85.00 $60.00

Suede Moccasin – Exmoor

(2)

Was $85.00 $49.00

Outdoor Mule – Burgundy

(8)

Was $85.00 $49.00

Prestige Suede Sneakers - Tan

(8)

Was $149.00 $70.00

Prestige Suede Sneakers - Gray

(5)

Was $149.00 $70.00

Prestige Suede Sneakers - Navy

(8)

Was $149.00 $70.00

Prestige Desert Boots - Gray

(2)

Was $159.00 $89.00

Prestige Lightweight Derby - Tan

(39)

Was $149.00 $85.00

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

(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 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

(46)

Was $159.00 $79.00

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

(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

(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 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

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

(187)

Was $159.00 $75.00

Prestige Bartlett Brogue - Tan

(143)

Was $159.00 $75.00

Prestige Brogue - Black

(169)

Was $159.00 $75.00

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

(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

(1486)

Was $159.00 $79.00

Prestige Chelsea Boot

(346)

Was $159.00 $79.00

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 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

(86)

Was $85.00 $49.00

Grecian Slipper - Black

(207)

Was $85.00 $49.00

Grecian Slipper - Brown

(204)

Was $85.00 $49.00

Albert Slipper - Black

(317)

Was $85.00 $49.00

Mule - Black

(240)

Was $85.00 $49.00

Albert Slipper - Brown

(274)

Was $85.00 $49.00

Mule - Brown

(122)

Was $85.00 $49.00

Albert Slipper - Oxblood

(200)

Was $85.00 $49.00

Fisherman's Sandals

(119)

Was $89.00 $49.00

Outdoor Mule - Black

(652)

Was $85.00 $49.00

Outdoor Mule - Brown

(1332)

Was $85.00 $49.00

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