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    All Men's Leather Shoes

    Handmade by master craftsmen, our men's leather shoes are comfortable, stylish, and designed to last. Whether you're looking for a pair of polished black Oxford shoes to wear with a suit, or a relaxed pair of brown brogues, good quality leather shoes from Samuel Windsor are a sound investment.

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    New

    Any 2 for $250

    Prestige Crepe Sole Chelsea Boots - Navy

    Prestige Crepe Sole Chelsea Boots - Navy

    (0)

    $150.00

    New

    Any 2 for $250

    Prestige Lightweight Derby - Tobacco

    Prestige Lightweight Derby - Tobacco

    (0)

    $140.00

    New

    Any 2 for $250

    Prestige Boat Shoe - Tan

    Prestige Boat Shoe - Tan

    (0)

    $140.00

    New

    Any 2 for $250

    Prestige Penny Loafer - Tan

    Prestige Penny Loafer - Tan

    (1)

    $140.00

    Any 2 for $210

    Classic Boat Shoe - Navy/Brown

    Classic Boat Shoe - Navy/Brown

    (119)

    $120.00

    Any 2 for $210

    Classic Boat Shoe - Blue

    Classic Boat Shoe - Blue

    (40)

    $120.00

    Any 2 for $210

    Classic Boat Shoe - Tobacco

    Classic Boat Shoe - Tobacco

    (44)

    $120.00

    Any 2 for $250

    Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (31)

    $140.00

    Any 2 for $210

    Classic Slip-On Boat Shoe - Navy/Brown

    Classic Slip-On Boat Shoe - Navy/Brown

    (422)

    $120.00

    Prestige Davington Brogue - Tan

    Prestige Davington Brogue - Tan

    (23)

    $145.00

    Prestige Chelsea Boots - Rubber Sole - Tan

    Prestige Chelsea Boots - Rubber Sole - Tan

    (24)

    $155.00

    Prestige Chukka Boots - Tan

    Prestige Chukka Boots - Tan

    (29)

    $155.00

    Any 2 for $210

    Classic Cheltenham Brogue In Suede - Mid Brown

    Classic Cheltenham Brogue In Suede - Mid Brown

    (61)

    $120.00

    Prestige Bartlett Brogue In Suede - Mid Brown

    Prestige Bartlett Brogue In Suede - Mid Brown

    (37)

    $145.00

    Any 2 for $210

    Classic Oxford Shoe - Tan

    Classic Oxford Shoe - Tan

    (396)

    $120.00

    Any 2 for $210

    Classic Chichester Shoe - Black

    Classic Chichester Shoe - Black

    (138)

    $130.00

    Prestige Suede Chelsea Boot - Black

    Prestige Suede Chelsea Boot - Black

    (17)

    $155.00

    Prestige Suede Chelsea Boot - Brown

    Prestige Suede Chelsea Boot - Brown

    (26)

    $155.00

    Prestige Monk Boot - Black

    Prestige Monk Boot - Black

    (31)

    $145.00

    Prestige Leyton Boot - Burgundy

    Prestige Leyton Boot - Burgundy

    (34)

    $145.00

    Prestige Country Boot - Black

    Prestige Country Boot - Black

    (83)

    $155.00

    Prestige Bartlett Brogue In Tweed

    Prestige Bartlett Brogue In Tweed

    (39)

    $160.00

    Prestige Country Boot In Tweed

    Prestige Country Boot In Tweed

    (39)

    $165.00

    Any 2 for $210

    Classic Oxblood Cheltenham Brogue

    Classic Oxblood Cheltenham Brogue

    (296)

    $120.00

    Prestige Whitworth Brogue - Black

    Prestige Whitworth Brogue - Black

    (81)

    $145.00

    Prestige Whitworth Brogue

    Prestige Whitworth Brogue

    (176)

    $145.00

    Prestige Bartlett Brogue - Tan

    Prestige Bartlett Brogue - Tan

    (133)

    $145.00

    Any 2 for $210

    Classic Suede Oxford Shoe

    Classic Suede Oxford Shoe

    (76)

    $120.00

    Any 2 for $210

    Classic Oxford Shoe - Oxblood

    Classic Oxford Shoe - Oxblood

    (340)

    $120.00

    Prestige Oxford Shoe - Rubber Sole

    Prestige Oxford Shoe - Rubber Sole

    (44)

    $145.00

    Any 2 for $250

    Prestige Dress Shoe - Black

    Prestige Dress Shoe - Black

    (241)

    $140.00

    Any 2 for $250

    Prestige Oxford Dress Shoe - Black

    Prestige Oxford Dress Shoe - Black

    (128)

    $140.00

    Prestige Cumbria Boot

    Prestige Cumbria Boot

    (187)

    $145.00

    Any 2 for $250

    Prestige Lace-Up Boat Shoe

    Prestige Lace-Up Boat Shoe

    (235)

    $140.00

    Any 2 for $250

    Prestige Leather Lace-Up Boat Shoe

    Prestige Leather Lace-Up Boat Shoe

    (394)

    $140.00

    Any 2 for $250

    Prestige Boat Shoe

    Prestige Boat Shoe

    (293)

    $140.00

    Any 2 for $210

    Classic Penny Loafer - Black Suede

    Classic Penny Loafer - Black Suede

    (75)

    $120.00

    Any 2 for $250

    Prestige Twin Monk Shoe - Oxblood

    Prestige Twin Monk Shoe - Oxblood

    (134)

    $140.00

    Any 2 for $210

    Classic Slip-On Boat Shoe

    Classic Slip-On Boat Shoe

    (422)

    $120.00

    Any 2 for $250

    Prestige Slip-On Boat Shoe

    Prestige Slip-On Boat Shoe

    (329)

    $140.00

    Any 2 for $250

    Prestige Slip-On Boat Shoe - Brown

    Prestige Slip-On Boat Shoe - Brown

    (338)

    $140.00

    Prestige Chelsea Boot - Black

    Prestige Chelsea Boot - Black

    (1477)

    $145.00

    Prestige Chelsea Boot

    Prestige Chelsea Boot

    (339)

    $145.00

    Any 2 for $250

    Prestige Oxford Shoe - Black

    Prestige Oxford Shoe - Black

    (802)

    $140.00

    Any 2 for $210

    Classic Semi-Brogue - Black

    Classic Semi-Brogue - Black

    (4129)

    $120.00

    Any 2 for $210

    Classic Boat Shoe

    Classic Boat Shoe

    (743)

    $120.00

    Any 2 for $210

    Classic Penny Loafer - Dark Brown Suede

    Classic Penny Loafer - Dark Brown Suede

    (380)

    $120.00

    Any 2 for $210

    Classic Oxford Shoe - Black

    Classic Oxford Shoe - Black

    (8301)

    $120.00

    Any 2 for $210

    Classic Penny Loafer - Brown Suede

    Classic Penny Loafer - Brown Suede

    (955)

    $120.00

    Any 2 for $250

    Prestige Semi-Brogue

    Prestige Semi-Brogue

    (588)

    $140.00

    Any 2 for $210

    Classic Durham Shoe - Black

    Classic Durham Shoe - Black

    (150)

    $120.00

    Samuel Windsor

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