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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 Outdoor Mule - Honey

Outdoor Mule - Honey

(1)

$49.00 $40.00 Save $9.00

Sale Outdoor Mule - Navy Nubuck

Outdoor Mule - Navy Nubuck

(1)

$49.00 $40.00 Save $9.00

Sale Outdoor Mule - Natural

Outdoor Mule - Natural

(3)

$49.00 $40.00 Save $9.00

Sale Leather Soled Sandal - Natural

Leather Soled Sandal - Natural

(0)

$49.00 $40.00 Save $9.00

Sale Leather Soled Sandal - Black

Leather Soled Sandal - Black

(0)

$49.00 $40.00 Save $9.00

Sale Leather Soled Sandal - Tan

Leather Soled Sandal - Tan

(1)

$49.00 $40.00 Save $9.00

Sale Strapless Sandal - Natural

Strapless Sandal - Natural

(1)

$49.00 $40.00 Save $9.00

Sale Prestige Tweed Brogue - Exmoor

Prestige Tweed Brogue - Exmoor

(7)

Was $189.00 $69.00 $60.00 Save $9.00

Sale Prestige Chiltern Boot – Dark Brown Waxed Suede

Prestige Chiltern Boot – Dark Brown Waxed Suede

(2)

Was $159.00 $69.00 $60.00 Save $9.00

Sale Prestige Tweed Brogue Boot – Dartmoor

Prestige Tweed Brogue Boot – Dartmoor

(1)

Was $189.00 $75.00 $65.00 Save $10.00

Sale Suede Moccasin – Dartmoor

Suede Moccasin – Dartmoor

(2)

Was $85.00 $60.00 $40.00 Save $20.00

Sale Suede Moccasin – Exmoor

Suede Moccasin – Exmoor

(3)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Outdoor Mule – Burgundy

Outdoor Mule – Burgundy

(10)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Prestige Suede Sneakers - Tan

Prestige Suede Sneakers - Tan

(8)

Was $149.00 $65.00 $55.00 Save $10.00

Sale Prestige Suede Sneakers - Gray

Prestige Suede Sneakers - Gray

(7)

Was $149.00 $65.00 $55.00 Save $10.00

Sale Prestige Suede Sneakers - Navy

Prestige Suede Sneakers - Navy

(10)

Was $149.00 $65.00 $55.00 Save $10.00

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

Sale

Any 2 pairs for $90

Prestige Boat Shoe - Gray

Prestige Boat Shoe - Gray

(410)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

(322)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Boat Shoe - Tan

Prestige Boat Shoe - Tan

(410)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Boat Shoe - Navy

Prestige Boat Shoe - Navy

(353)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Penny Loafer - Tan

Prestige Penny Loafer - Tan

(266)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Boat Shoe - Dark Olive

Prestige Boat Shoe - Dark Olive

(353)

Was $149.00 $75.00 $50.00 Save $25.00

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

Sale

Any 2 Pairs For $80

Classic Boat Shoe - Blue

Classic Boat Shoe - Blue

(45)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Boat Shoe - Tobacco

Classic Boat Shoe - Tobacco

(46)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(131)

Was $135.00 $55.00 $45.00 Save $10.00

Sale Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(39)

Was $149.00 $45.00

Sale

Any 2 Pairs 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 Pairs 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

Sale

Any 2 Pairs For $80

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(12)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(19)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(58)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(167)

Was $135.00 $55.00 $45.00 Save $10.00

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

(31)

Was $189.00 $69.00 $60.00 Save $9.00

Sale Prestige Davington Brogue - Tan

Prestige Davington Brogue - Tan

(27)

Was $159.00 $65.00 $55.00 Save $10.00

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

Sale Prestige Chiltern Boot - Brown

Prestige Chiltern Boot - Brown

(47)

Was $159.00 $69.00 $60.00 Save $9.00

Sale Prestige Chiltern Boot - Nubuck

Prestige Chiltern Boot - Nubuck

(13)

Was $159.00 $69.00 $60.00 Save $9.00

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 - 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 Pairs For $100

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(70)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 Pairs For $80

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(167)

Was $135.00 $55.00 $45.00 Save $10.00

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 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

(106)

Was $189.00 $85.00 $80.00 Save $5.00

Prestige Whitworth Brogue - Navy

(33)

Was $159.00 $99.00

Sale

Any 2 Pairs For $80

Classic Monk Shoe - Black

Classic Monk Shoe - Black

(2441)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Monk Shoe - Brown

Classic Monk Shoe - Brown

(1667)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(4123)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Penny Loafer - Brown

Classic Penny Loafer - Brown

(2126)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Oxford Shoe - Brown

Classic Oxford Shoe - Brown

(2527)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(316)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $100

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(79)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 Pairs For $80

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(370)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs 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

(179)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 Pairs For $100

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1334)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 Pairs For $80

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(83)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Monk Brogue - Black

Classic Monk Brogue - Black

(285)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

(431)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4136)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Boat Shoe

Classic Boat Shoe

(750)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Penny Loafer - Dark Brown Suede

Classic Penny Loafer - Dark Brown Suede

(386)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Penny Loafer - Brown Suede

Classic Penny Loafer - Brown Suede

(961)

Was $135.00 $75.00 $45.00 Save $30.00

Sale

Any 2 Pairs For $80

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8339)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1787)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(3251)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(2089)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Kempton Shoe

Classic Kempton Shoe

(2654)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 pairs for $90

Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

(605)

Was $149.00 $65.00 $50.00 Save $15.00

Sale Prestige Oxford Shoe - Rubber Sole - Black

Prestige Oxford Shoe - Rubber Sole - Black

(2330)

Was $159.00 $65.00 $55.00 Save $10.00

Sale

Any 2 pairs for $90

Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

(134)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

(247)

Was $149.00 $65.00 $50.00 Save $15.00

Sale Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

(86)

Was $159.00 $85.00 $72.50 Save $12.50

Sale Prestige Whitworth Brogue

Prestige Whitworth Brogue

(187)

Was $159.00 $65.00 $55.00 Save $10.00

Sale Prestige Bartlett Brogue - Tan

Prestige Bartlett Brogue - Tan

(143)

Was $159.00 $65.00 $55.00 Save $10.00

Sale Prestige Brogue - Black

Prestige Brogue - Black

(170)

Was $159.00 $65.00 $55.00 Save $10.00

Sale Prestige Split Brogue - Brown

Prestige Split Brogue - Brown

(188)

Was $159.00 $65.00 $55.00 Save $10.00

Sale Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

(47)

Was $179.00 $45.00

Sale Prestige Oxford - Black

Prestige Oxford - Black

(229)

Was $159.00 $65.00 $55.00 Save $10.00

Sale Prestige Country Brogue - Rubber Sole

Prestige Country Brogue - Rubber Sole

(325)

Was $179.00 $85.00 $72.50 Save $12.50

Sale

Any 2 pairs for $90

Prestige Leather Lace-Up Boat Shoe

Prestige Leather Lace-Up Boat Shoe

(410)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Boat Shoe

Prestige Boat Shoe

(313)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Lace-Up Boat Shoe

Prestige Lace-Up Boat Shoe

(243)

Was $149.00 $65.00 $50.00 Save $15.00

Sale Prestige Cumbria Boot

Prestige Cumbria Boot

(191)

Was $159.00 $85.00 $80.00 Save $5.00

Sale

Any 2 pairs for $90

Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

(148)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Twin Monk - Black

Prestige Twin Monk - Black

(188)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Slip-On Boat Shoe - Brown

Prestige Slip-On Boat Shoe - Brown

(353)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Slip-On Boat Shoe

Prestige Slip-On Boat Shoe

(340)

Was $149.00 $65.00 $50.00 Save $15.00

Sale Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

(322)

Was $149.00 $50.00

Sale Prestige Penny Loafer

Prestige Penny Loafer

(266)

Was $149.00 $50.00

Sale Prestige Semi-Brogue

Prestige Semi-Brogue

(592)

Was $149.00 $50.00

Sale

Any 2 pairs for $90

Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

(810)

Was $149.00 $65.00 $50.00 Save $15.00

Sale Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

(1488)

Was $159.00 $69.00 $55.00 Save $14.00

Sale Prestige Chelsea Boot

Prestige Chelsea Boot

(345)

Was $159.00 $69.00 $55.00 Save $14.00

Sale Prestige Suede Chelsea Boot

Prestige Suede Chelsea Boot

(764)

Was $159.00 $69.00 $55.00 Save $14.00

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

(275)

Was $189.00 $85.00 $80.00 Save $5.00

Sale Grecian Slipper - Navy

Grecian Slipper - Navy

(87)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Grecian Slipper - Black

Grecian Slipper - Black

(207)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Grecian Slipper - Brown

Grecian Slipper - Brown

(206)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Albert Slipper - Black

Albert Slipper - Black

(319)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Mule - Black

Mule - Black

(243)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Albert Slipper - Brown

Albert Slipper - Brown

(275)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Mule - Brown

Mule - Brown

(124)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Albert Slipper - Oxblood

Albert Slipper - Oxblood

(206)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Handmade Leather Sandal - Single Cross - Tan

Handmade Leather Sandal - Single Cross - Tan

(51)

Was $89.00 $49.00 $40.00 Save $9.00

Sale Handmade Leather Sandal - Touch Fasten - Brown

Handmade Leather Sandal - Touch Fasten - Brown

(96)

Was $89.00 $49.00 $40.00 Save $9.00

Sale Fisherman's Sandals

Fisherman's Sandals

(121)

Was $89.00 $49.00 $40.00 Save $9.00

Sale Churchill Fleece Lined Outdoor Mule - Brown

Churchill Fleece Lined Outdoor Mule - Brown

(233)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Outdoor Mule - Black

Outdoor Mule - Black

(658)

Was $85.00 $49.00 $40.00 Save $9.00

Sale Outdoor Mule - Brown

Outdoor Mule - Brown

(1341)

Was $85.00 $49.00 $40.00 Save $9.00

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