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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.

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe - Brown

Prestige Slip-On Boat Shoe - Brown

(1)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Tasselled Loafer - Sand
Sale

Any 2 pairs for $120

Classic Boat Shoe - Blue

Classic Boat Shoe - Blue

(28)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Boat Shoe - Tobacco

Classic Boat Shoe - Tobacco

(32)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(72)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Lightweight Oxford - Brown

Prestige Lightweight Oxford - Brown

(21)

$79.00 $70.00 Save $9.00

Sale Prestige Suede Chelsea Boot - Navy

Prestige Suede Chelsea Boot - Navy

(30)

$85.00 $79.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Lightweight Brogue - Navy

Prestige Lightweight Brogue - Navy

(15)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Lightweight Brogue - Sand

Prestige Lightweight Brogue - Sand

(22)

$79.00 $70.00 Save $9.00

Sale Prestige Penny Loafer Suede - Navy

Prestige Penny Loafer Suede - Navy

(59)

$85.00 $79.00 Save $6.00

Sale Prestige Penny Loafer Suede - Brown

Prestige Penny Loafer Suede - Brown

(43)

$85.00 $79.00 Save $6.00

Sale Prestige Suede Chelsea Boot - Sand

Prestige Suede Chelsea Boot - Sand

(16)

$85.00 $79.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(18)

$79.00 $70.00 Save $9.00

Sale Classic Leather Driving Shoe

Classic Leather Driving Shoe

(50)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Driving Shoe - Navy/Brown

Prestige Driving Shoe - Navy/Brown

(28)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $120

Classic Moccasin

Classic Moccasin

(108)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Moccasin - Brown

Classic Moccasin - Brown

(25)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Suede Driving Shoe

Classic Suede Driving Shoe

(106)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Penny Loafer - Suede - Black

Prestige Penny Loafer - Suede - Black

(12)

$89.00 $70.00 Save $19.00

Sale

Any 2 pairs for $120

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(35)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(66)

$69.00 $65.00 Save $4.00

Sale Prestige Bartlett Brogue In Suede - Mid Brown

Prestige Bartlett Brogue In Suede - Mid Brown

(7)

$85.00 $79.00 Save $6.00

Sale

Any 2 pairs for $120

Classic Monk Shoe - Black

Classic Monk Shoe - Black

(2382)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Monk Shoe - Brown

Classic Monk Shoe - Brown

(1627)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(4037)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Brown

Classic Penny Loafer - Brown

(2096)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Semi-Brogue

Classic Semi-Brogue

(1661)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Brown

Classic Oxford Shoe - Brown

(2449)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(205)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(62)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(241)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Mid-Brown

Classic Oxford Shoe - Mid-Brown

(168)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Tan

Classic Oxford Shoe - Tan

(345)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

(122)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1303)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Tan Cheltenham Brogue

Classic Tan Cheltenham Brogue

(157)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(56)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Monk Brogue - Black

Classic Monk Brogue - Black

(232)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

(385)

$69.00 $65.00 Save $4.00

Any 2 pairs for $120

Classic Semi-Brogue - Black
Sale

Any 2 pairs for $120

Classic Boat Shoe

Classic Boat Shoe

(697)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Dark Brown Suede

Classic Penny Loafer - Dark Brown Suede

(357)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Brown Suede

Classic Penny Loafer - Brown Suede

(939)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8100)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1757)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(3095)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic City Shoe - Black

Classic City Shoe - Black

(2916)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(2031)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $120

Classic Kempton Shoe

Classic Kempton Shoe

(2581)

$69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

(582)

$79.00 $70.00 Save $9.00

Sale Prestige Oxford Shoe - Rubber Sole - Black

Prestige Oxford Shoe - Rubber Sole - Black

(2251)

$85.00 $79.00 Save $6.00

Sale Prestige Brogue - Rubber Sole

Prestige Brogue - Rubber Sole

(734)

$85.00 $79.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

(219)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

(92)

$79.00 $70.00 Save $9.00

Sale Prestige Whitworth Brogue

Prestige Whitworth Brogue

(125)

$85.00 $79.00 Save $6.00

Sale Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

(56)

$85.00 $79.00 Save $6.00

Sale Prestige Bartlett Brogue - Tan

Prestige Bartlett Brogue - Tan

(89)

$85.00 $79.00 Save $6.00

Sale Prestige Split Brogue - Two-Tone

Prestige Split Brogue - Two-Tone

(53)

$85.00 $79.00 Save $6.00

Sale Prestige Split Brogue - Brown

Prestige Split Brogue - Brown

(154)

$85.00 $79.00 Save $6.00

Sale Prestige Brogue - Black

Prestige Brogue - Black

(149)

$85.00 $79.00 Save $6.00

Sale Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

(20)

$85.00 $79.00 Save $6.00

Sale Prestige Oxford - Black

Prestige Oxford - Black

(198)

$85.00 $79.00 Save $6.00

Sale Prestige Brogue - Rubber Sole - Black

Prestige Brogue - Rubber Sole - Black

(545)

$85.00 $79.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Leather Lace-Up Boat Shoe

Prestige Leather Lace-Up Boat Shoe

(371)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Lace-Up Boat Shoe

Prestige Lace-Up Boat Shoe

(224)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe

Prestige Boat Shoe

(225)

$79.00 $70.00 Save $9.00

Sale Prestige Cumbria Boot

Prestige Cumbria Boot

(171)

$85.00 $79.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Tasselled Suede Loafer

Prestige Tasselled Suede Loafer

(290)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

(77)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Twin Monk - Black

Prestige Twin Monk - Black

(130)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe - Brown

Prestige Slip-On Boat Shoe - Brown

(323)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe - Green

Prestige Slip-On Boat Shoe - Green

(317)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

(286)

$79.00 $70.00 Save $9.00

Sale Prestige Penny Loafer

Prestige Penny Loafer

(233)

$75.00 $70.00 Save $5.00

Sale

Any 2 pairs for $130

Prestige Semi-Brogue

Prestige Semi-Brogue

(576)

$79.00 $70.00 Save $9.00

Sale

Any 2 pairs for $130

Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

(777)

$79.00 $70.00 Save $9.00

Sale Prestige Chelsea Boot

Prestige Chelsea Boot

(310)

$85.00 $79.00 Save $6.00

Sale Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

(1421)

$85.00 $79.00 Save $6.00

Sale Prestige Suede Chelsea Boot

Prestige Suede Chelsea Boot

(727)

$85.00 $79.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Semi-Brogue - Black

Prestige Semi-Brogue - Black

(846)

$79.00 $70.00 Save $9.00

Sale Prestige Belgravia Shoe

Prestige Belgravia Shoe

(198)

$85.00 $79.00 Save $6.00

Sale Outdoor Mule - Black

Outdoor Mule - Black

(33)

$40.00

Sale Outdoor Mule - Brown

Outdoor Mule - Brown

(33)

$40.00

Sale Albert Slipper - Black

Albert Slipper - Black

(268)

$52.50 $45.00 Save $7.50

Sale Albert Slipper - Brown

Albert Slipper - Brown

(252)

$52.50 $45.00 Save $7.50

Sale Albert Slipper - Oxblood

Albert Slipper - Oxblood

(119)

$52.50 $45.00 Save $7.50

Sale Mule - Black

Mule - Black

(186)

$52.50 $45.00 Save $7.50

Sale Mule - Brown

Mule - Brown

(97)

$52.50 $45.00 Save $7.50

Sale Grecian Slipper - Navy

Grecian Slipper - Navy

(61)

$52.50 $45.00 Save $7.50

Sale Grecian Slipper - Black

Grecian Slipper - Black

(172)

$52.50 $45.00 Save $7.50

Sale Grecian Slipper - Brown

Grecian Slipper - Brown

(174)

$52.50 $45.00 Save $7.50

Sale Handmade Leather Sandal - Single Cross - Tan

Handmade Leather Sandal - Single Cross - Tan

(35)

$55.00 $45.00 Save $10.00

Sale Handmade Leather Sandal - Touch Fasten - Brown

Handmade Leather Sandal - Touch Fasten - Brown

(77)

$55.00 $45.00 Save $10.00

Sale Fisherman's Sandals

Fisherman's Sandals

(108)

$55.00 $45.00 Save $10.00

Sale Outdoor Mule - Black

Outdoor Mule - Black

(547)

$52.50 $45.00 Save $7.50

Sale Outdoor Mule - Brown

Outdoor Mule - Brown

(1099)

$52.50 $45.00 Save $7.50

Sale Churchill Fleece Lined Outdoor Mule - Brown

Churchill Fleece Lined Outdoor Mule - Brown

(189)

$52.50 $45.00 Save $7.50

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