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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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Sale

Any 2 pairs for $130

Prestige Suede Sneakers - Gray

Prestige Suede Sneakers - Gray

(2)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Suede Sneakers - Navy

Prestige Suede Sneakers - Navy

(5)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Suede Sneakers - Tan

Prestige Suede Sneakers - Tan

(2)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Crepe Sole Chelsea Boots - Tan

Prestige Crepe Sole Chelsea Boots - Tan

(0)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Crepe Sole Chelsea Boots - Navy

Prestige Crepe Sole Chelsea Boots - Navy

(0)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Crepe Sole Desert Boots - Tan

Prestige Crepe Sole Desert Boots - Tan

(0)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Crepe Sole Desert Boots - Navy

Prestige Crepe Sole Desert Boots - Navy

(1)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Desert Boots - Gray

Prestige Desert Boots - Gray

(0)

Was $159.00 $85.00 $75.00 Save $10.00

Sale

Any 2 pairs for $130

Prestige Lightweight Derby - Navy Suede

Prestige Lightweight Derby - Navy Suede

(32)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(32)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Lightweight Derby - Tobacco

Prestige Lightweight Derby - Tobacco

(39)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Gray

Prestige Boat Shoe - Gray

(399)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

(315)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Navy

Prestige Boat Shoe - Navy

(341)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Tan

Prestige Boat Shoe - Tan

(399)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Penny Loafer - Tan

Prestige Penny Loafer - Tan

(257)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Dark Olive

Prestige Boat Shoe - Dark Olive

(341)

Was $149.00 $75.00 $69.00 Save $6.00

Prestige Tasselled Loafer - Sand

(30)

Was $149.00 $50.00

Sale

Any 2 pairs for $120

Classic Lightweight Brogue - Navy

Classic Lightweight Brogue - Navy

(41)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Boat Shoe - Blue

Classic Boat Shoe - Blue

(41)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Boat Shoe - Tobacco

Classic Boat Shoe - Tobacco

(45)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(121)

Was $135.00 $65.00

Prestige Lightweight Oxford - Brown

(32)

Was $149.00 $50.00

Prestige Suede Chelsea Boot - Navy

(59)

Was $159.00 $59.00

Sale Prestige Penny Loafer Suede - Brown

Prestige Penny Loafer Suede - Brown

(52)

Was $159.00 $45.00

Sale Prestige Penny Loafer Suede - Navy

Prestige Penny Loafer Suede - Navy

(94)

Was $159.00 $45.00

Sale Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(32)

Was $149.00 $45.00

Sale

Any 2 pairs for $120

Classic Moccasin

Classic Moccasin

(119)

Was $135.00 $65.00

Sale Classic Leather Driving Shoe

Classic Leather Driving Shoe

(84)

Was $135.00 $40.00

Sale Prestige Driving Shoe - Navy/Brown

Prestige Driving Shoe - Navy/Brown

(39)

Was $149.00 $45.00

Sale

Any 2 pairs for $120

Classic Suede Driving Shoe

Classic Suede Driving Shoe

(109)

Was $135.00 $65.00

Sale Prestige Penny Loafer - Suede - Black

Prestige Penny Loafer - Suede - Black

(27)

Was $159.00 $45.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(11)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(39)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(6)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(142)

Was $135.00 $65.00 $62.50 Save $2.50

Sale Prestige Derby Shoe - Tan

Prestige Derby Shoe - Tan

(15)

Was $159.00 $45.00

Sale Prestige Chelsea Boot - Rubber Sole - Black

Prestige Chelsea Boot - Rubber Sole - Black

(28)

Was $189.00 $95.00 $79.00 Save $16.00

Sale Prestige Twin Monk Shoe - Tan

Prestige Twin Monk Shoe - Tan

(174)

Was $149.00 $45.00

Sale Prestige Davington Brogue - Tan

Prestige Davington Brogue - Tan

(24)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Fairfield Boots - Brown

Prestige Fairfield Boots - Brown

(21)

Was $159.00 $50.00

Sale Prestige Country Boot - Navy

Prestige Country Boot - Navy

(266)

Was $189.00 $85.00 $75.00 Save $10.00

Sale Prestige Fairfield Boot - Black

Prestige Fairfield Boot - Black

(94)

Was $159.00 $50.00

Sale Prestige Belgravia Boot - Black

Prestige Belgravia Boot - Black

(222)

Was $159.00 $50.00

Sale Prestige Chukka Boot - Black

Prestige Chukka Boot - Black

(21)

Was $189.00 $85.00 $79.00 Save $6.00

Sale Prestige Chukka Boot - Suede

Prestige Chukka Boot - Suede

(12)

Was $189.00 $95.00 $79.00 Save $16.00

Sale Prestige Chiltern Boot - Brown

Prestige Chiltern Boot - Brown

(40)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Chiltern Boot - Nubuck

Prestige Chiltern Boot - Nubuck

(12)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Chukka Boots - Tan

Prestige Chukka Boots - Tan

(29)

Was $189.00 $95.00 $79.00 Save $16.00

Sale Prestige Davington Brogue - Black

Prestige Davington Brogue - Black

(22)

Was $159.00 $80.00 $75.00 Save $5.00

Prestige Whitworth Brogue - Tan

(181)

Was $159.00 $75.00

Sale Prestige Oxford Shoe - Tan

Prestige Oxford Shoe - Tan

(7)

Was $159.00 $45.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe - Navy/Brown

Classic Slip-On Boat Shoe - Navy/Brown

(425)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe - Camel

Classic Slip-On Boat Shoe - Camel

(425)

Was $135.00 $65.00

Sale Prestige Boat Shoe - Navy

Prestige Boat Shoe - Navy

(300)

Was $149.00 $40.00

Sale Classic Lightweight Brogue - Sand

Classic Lightweight Brogue - Sand

(39)

Was $135.00 $45.00

Sale

Any 2 pairs for $120

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(64)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(142)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Tan

Classic Oxford Shoe - Tan

(399)

Was $135.00 $65.00 $62.50 Save $2.50

Sale Prestige Suede Chelsea Boot - Black

Prestige Suede Chelsea Boot - Black

(18)

Was $189.00 $55.00

Sale Prestige Suede Chelsea Boot - Brown

Prestige Suede Chelsea Boot - Brown

(30)

Was $189.00 $50.00

Prestige Leyton Boot - Burgundy

(34)

Was $159.00 $59.00

Sale Prestige Monk Boot - Black

Prestige Monk Boot - Black

(32)

Was $159.00 $50.00

Sale Prestige Country Boot - Black

Prestige Country Boot - Black

(94)

Was $189.00 $55.00

Sale

Any 2 pairs for $120

Classic Monk Shoe - Black

Classic Monk Shoe - Black

(2428)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Monk Shoe - Brown

Classic Monk Shoe - Brown

(1662)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(4118)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Brown

Classic Penny Loafer - Brown

(2120)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Brown

Classic Oxford Shoe - Brown

(2518)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(303)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(76)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(343)

Was $135.00 $65.00 $62.50 Save $2.50

Classic Oxford Shoe - Mid-Brown

(195)

Was $135.00 $45.00

Sale

Any 2 pairs for $120

Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

(149)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Tan Cheltenham Brogue

Classic Tan Cheltenham Brogue

(177)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1331)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(75)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Monk Brogue - Black

Classic Monk Brogue - Black

(280)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

(425)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4130)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Boat Shoe

Classic Boat Shoe

(747)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Dark Brown Suede

Classic Penny Loafer - Dark Brown Suede

(383)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Brown Suede

Classic Penny Loafer - Brown Suede

(955)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8310)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1781)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(3231)

Was $135.00 $65.00 $62.50 Save $2.50

Sale Classic City Shoe - Black

Classic City Shoe - Black

(2950)

Was $135.00 $40.00

Sale

Any 2 pairs for $120

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(2081)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Kempton Shoe

Classic Kempton Shoe

(2644)

Was $135.00 $70.00 $65.00 Save $5.00

Sale Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

(599)

Was $149.00 $50.00

Sale Prestige Oxford Shoe - Rubber Sole - Black

Prestige Oxford Shoe - Rubber Sole - Black

(2326)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Brogue - Rubber Sole

Prestige Brogue - Rubber Sole

(766)

Was $159.00 $50.00

Sale

Any 2 pairs for $130

Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

(242)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

(129)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

(84)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Whitworth Brogue

Prestige Whitworth Brogue

(181)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Bartlett Brogue - Tan

Prestige Bartlett Brogue - Tan

(135)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Brogue - Black

Prestige Brogue - Black

(168)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Split Brogue - Brown

Prestige Split Brogue - Brown

(179)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

(45)

Was $179.00 $45.00

Sale Prestige Oxford - Black

Prestige Oxford - Black

(226)

Was $159.00 $85.00 $75.00 Save $10.00

Sale

Any 2 pairs for $130

Prestige Lace-Up Boat Shoe

Prestige Lace-Up Boat Shoe

(237)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Leather Lace-Up Boat Shoe

Prestige Leather Lace-Up Boat Shoe

(399)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe

Prestige Boat Shoe

(300)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Cumbria Boot

Prestige Cumbria Boot

(187)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Tasselled Suede Loafer

Prestige Tasselled Suede Loafer

(308)

Was $149.00 $45.00

Sale

Any 2 pairs for $130

Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

(137)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Twin Monk - Black

Prestige Twin Monk - Black

(174)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe

Prestige Slip-On Boat Shoe

(331)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe - Brown

Prestige Slip-On Boat Shoe - Brown

(341)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

(315)

Was $149.00 $50.00

Sale Prestige Penny Loafer

Prestige Penny Loafer

(257)

Was $149.00 $50.00

Sale Prestige Semi-Brogue

Prestige Semi-Brogue

(588)

Was $149.00 $50.00

Sale

Any 2 pairs for $130

Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

(802)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

(1480)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Chelsea Boot

Prestige Chelsea Boot

(342)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Suede Chelsea Boot

Prestige Suede Chelsea Boot

(759)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Semi-Brogue - Black

Prestige Semi-Brogue - Black

(866)

Was $149.00 $50.00

Prestige Belgravia Shoe

(222)

Was $159.00 $79.00

Sale Prestige Country Boot - Rubber Sole - Tan

Grecian Slipper - Navy

(70)

Was $85.00 $55.00

Grecian Slipper - Black

(190)

Was $85.00 $55.00

Grecian Slipper - Brown

(193)

Was $85.00 $55.00

Albert Slipper - Black

(291)

Was $85.00 $55.00

Mule - Black

(215)

Was $85.00 $55.00

Albert Slipper - Brown

(262)

Was $85.00 $55.00

Mule - Brown

(107)

Was $85.00 $55.00

Albert Slipper - Oxblood

(162)

Was $85.00 $55.00

Fisherman's Sandals

(117)

Was $89.00 $55.00

Outdoor Mule - Black

(606)

Was $85.00 $55.00

Outdoor Mule - Brown

(1255)

Was $85.00 $55.00

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