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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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    Sale Prestige Crepe Sole Chelsea Boots - Navy

    Prestige Crepe Sole Chelsea Boots - Navy

    (0)

    $150.00 $130.00 Save $20.00

    Any 2 for $210

    Prestige Lightweight Derby - Tobacco

    Prestige Lightweight Derby - Tobacco

    (40)

    $140.00

    Any 2 for $210

    Prestige Boat Shoe - Tan

    Prestige Boat Shoe - Tan

    (401)

    $140.00

    Any 2 for $210

    Prestige Penny Loafer - Tan

    Prestige Penny Loafer - Tan

    (259)

    $140.00

    Sale

    Any 2 for $180

    Classic Boat Shoe - Navy/Brown

    Classic Boat Shoe - Navy/Brown

    (127)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Boat Shoe - Blue

    Classic Boat Shoe - Blue

    (42)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Boat Shoe - Tobacco

    Classic Boat Shoe - Tobacco

    (45)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (33)

    $140.00 $125.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Slip-On Boat Shoe - Navy/Brown

    Classic Slip-On Boat Shoe - Navy/Brown

    (427)

    $120.00 $105.00 Save $15.00

    Prestige Davington Brogue - Tan

    Prestige Davington Brogue - Tan

    (25)

    $145.00

    Prestige Chelsea Boots - Rubber Sole - Tan

    Prestige Chelsea Boots - Rubber Sole - Tan

    (31)

    $155.00

    Prestige Chukka Boots - Tan

    Prestige Chukka Boots - Tan

    (29)

    $155.00

    Any 2 for $210

    Prestige Slip-On Boat Shoe - Brown

    Prestige Slip-On Boat Shoe - Brown

    (19)

    $140.00

    Sale

    Any 2 for $180

    Classic Cheltenham Brogue In Suede - Mid Brown

    Classic Cheltenham Brogue In Suede - Mid Brown

    (65)

    $120.00 $105.00 Save $15.00

    Sale Prestige Bartlett Brogue In Suede - Mid Brown

    Prestige Bartlett Brogue In Suede - Mid Brown

    (37)

    $145.00 $130.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Oxford Shoe - Tan

    Classic Oxford Shoe - Tan

    (400)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Chichester Shoe - Black

    Classic Chichester Shoe - Black

    (146)

    $130.00 $105.00 Save $25.00

    Sale Prestige Suede Chelsea Boot - Black

    Prestige Suede Chelsea Boot - Black

    (21)

    $155.00 $140.00 Save $15.00

    Sale Prestige Suede Chelsea Boot - Brown

    Prestige Suede Chelsea Boot - Brown

    (36)

    $155.00 $140.00 Save $15.00

    Sale Prestige Monk Boot - Black

    Prestige Monk Boot - Black

    (32)

    $145.00 $130.00 Save $15.00

    Sale Prestige Leyton Boot - Burgundy

    Prestige Leyton Boot - Burgundy

    (34)

    $145.00 $130.00 Save $15.00

    Sale Prestige Country Boot - Black

    Prestige Country Boot - Black

    (98)

    $155.00 $140.00 Save $15.00

    Sale Prestige Bartlett Brogue In Tweed

    Prestige Bartlett Brogue In Tweed

    (44)

    $160.00 $145.00 Save $15.00

    Sale Prestige Country Boot In Tweed

    Prestige Country Boot In Tweed

    (41)

    $165.00 $150.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Oxblood Cheltenham Brogue

    Classic Oxblood Cheltenham Brogue

    (306)

    $120.00 $105.00 Save $15.00

    Sale Prestige Whitworth Brogue - Black

    Prestige Whitworth Brogue - Black

    (85)

    $145.00 $130.00 Save $15.00

    Sale Prestige Whitworth Brogue

    Prestige Whitworth Brogue

    (183)

    $145.00 $130.00 Save $15.00

    Sale Prestige Bartlett Brogue - Tan

    Prestige Bartlett Brogue - Tan

    (136)

    $145.00 $130.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Suede Oxford Shoe

    Classic Suede Oxford Shoe

    (78)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Oxford Shoe - Oxblood

    Classic Oxford Shoe - Oxblood

    (348)

    $120.00 $105.00 Save $15.00

    Sale Prestige Oxford Shoe - Rubber Sole

    Prestige Oxford Shoe - Rubber Sole

    (46)

    $145.00 $130.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Dress Shoe - Black

    Prestige Dress Shoe - Black

    (243)

    $140.00 $125.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Oxford Dress Shoe - Black

    Prestige Oxford Dress Shoe - Black

    (129)

    $140.00 $125.00 Save $15.00

    Sale Prestige Cumbria Boot

    Prestige Cumbria Boot

    (188)

    $145.00 $130.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Lace-Up Deck Shoe

    Prestige Lace-Up Deck Shoe

    (241)

    $140.00 $125.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Leather Lace-Up Deck Shoe

    Prestige Leather Lace-Up Deck Shoe

    (401)

    $140.00 $125.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Deck Shoe

    Prestige Deck Shoe

    (305)

    $140.00 $125.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Penny Loafer - Black Suede

    Classic Penny Loafer - Black Suede

    (76)

    $42.50

    Sale

    Any 2 for $210

    Prestige Twin Monk Shoe - Oxblood

    Prestige Twin Monk Shoe - Oxblood

    (140)

    $140.00 $125.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Slip-On Deck Shoe

    Classic Slip-On Deck Shoe

    (427)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Slip-On Boat Shoe

    Prestige Slip-On Boat Shoe

    (334)

    $140.00 $125.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Slip-On Deck Shoe - Brown

    Prestige Slip-On Deck Shoe - Brown

    (346)

    $140.00 $125.00 Save $15.00

    Sale Prestige Chelsea Boot - Black

    Prestige Chelsea Boot - Black

    (1480)

    $145.00 $130.00 Save $15.00

    Sale Prestige Chelsea Boot

    Prestige Chelsea Boot

    (342)

    $145.00 $130.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Oxford Shoe - Black

    Prestige Oxford Shoe - Black

    (804)

    $140.00 $125.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Semi-Brogue - Black

    Classic Semi-Brogue - Black

    (4133)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Deck Shoe

    Classic Deck Shoe

    (751)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Penny Loafer - Dark Brown Suede

    Classic Penny Loafer - Dark Brown Suede

    (383)

    $42.50

    Sale

    Any 2 for $180

    Classic Oxford Shoe - Black

    Classic Oxford Shoe - Black

    (8319)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $180

    Classic Penny Loafer - Brown Suede

    Classic Penny Loafer - Brown Suede

    (957)

    $120.00 $105.00 Save $15.00

    Sale

    Any 2 for $210

    Prestige Semi-Brogue

    Prestige Semi-Brogue

    (590)

    $140.00 $125.00 Save $15.00

    Samuel Windsor

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