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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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    Prestige Tweed Brogue - Exmoor

    Prestige Tweed Brogue - Exmoor

    (5)

    $145.00

    Prestige Tweed Brogue Boot – Dartmoor

    Prestige Tweed Brogue Boot – Dartmoor

    (0)

    $150.00

    Sale Prestige Crepe Sole Chelsea Boots - Navy

    Prestige Crepe Sole Chelsea Boots - Navy

    (0)

    $150.00 $125.00 Save $25.00

    Any 2 for $190

    Prestige Lightweight Derby - Tobacco

    Prestige Lightweight Derby - Tobacco

    (41)

    $125.00

    Sale

    Any 2 for $190

    Prestige Boat Shoe - Tan

    Prestige Boat Shoe - Tan

    (406)

    $125.00 $115.00 Save $10.00

    Sale

    Any 2 for $190

    Prestige Penny Loafer - Tan

    Prestige Penny Loafer - Tan

    (263)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Boat Shoe - Navy/Brown

    Classic Boat Shoe - Navy/Brown

    (130)

    $120.00 $95.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Boat Shoe - Tobacco

    Classic Boat Shoe - Tobacco

    (45)

    $120.00 $95.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Boat Shoe - Blue

    Classic Boat Shoe - Blue

    (43)

    $120.00 $95.00 Save $25.00

    Sale

    Any 2 for $190

    Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (39)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Slip-On Boat Shoe - Navy/Brown

    Classic Slip-On Boat Shoe - Navy/Brown

    (431)

    $120.00 $95.00 Save $25.00

    Prestige Davington Brogue - Tan

    Prestige Davington Brogue - Tan

    (27)

    $130.00

    Prestige Chelsea Boots - Rubber Sole - Tan

    Prestige Chelsea Boots - Rubber Sole - Tan

    (34)

    $130.00

    Prestige Chukka Boots - Tan

    Prestige Chukka Boots - Tan

    (33)

    $130.00

    Any 2 for $190

    Prestige Slip-On Boat Shoe - Brown

    Prestige Slip-On Boat Shoe - Brown

    (19)

    $125.00

    Sale

    Any 2 for $160

    Classic Cheltenham Brogue In Suede - Mid Brown

    Classic Cheltenham Brogue In Suede - Mid Brown

    (69)

    $120.00 $95.00 Save $25.00

    Sale Prestige Bartlett Brogue In Suede - Mid Brown

    Prestige Bartlett Brogue In Suede - Mid Brown

    (38)

    $145.00 $125.00 Save $20.00

    Sale

    Any 2 for $160

    Classic Oxford Shoe - Tan

    Classic Oxford Shoe - Tan

    (400)

    $120.00 $95.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Chichester Shoe - Black

    Classic Chichester Shoe - Black

    (162)

    $130.00 $95.00 Save $35.00

    Sale Prestige Suede Chelsea Boot - Black

    Prestige Suede Chelsea Boot - Black

    (27)

    $155.00 $140.00 Save $15.00

    Sale Prestige Suede Chelsea Boot - Brown

    Prestige Suede Chelsea Boot - Brown

    (40)

    $155.00 $140.00 Save $15.00

    Sale Prestige Monk Boot - Black

    Prestige Monk Boot - Black

    (34)

    $145.00 $125.00 Save $20.00

    Sale Prestige Country Boot - Black

    Prestige Country Boot - Black

    (104)

    $130.00

    Sale Prestige Bartlett Brogue In Tweed

    Prestige Bartlett Brogue In Tweed

    (46)

    $160.00 $140.00 Save $20.00

    Sale Prestige Country Boot In Tweed

    Prestige Country Boot In Tweed

    (41)

    $165.00 $145.00 Save $20.00

    Sale

    Any 2 for $160

    Classic Oxblood Cheltenham Brogue

    Classic Oxblood Cheltenham Brogue

    (313)

    $120.00 $95.00 Save $25.00

    Sale Prestige Whitworth Brogue - Black

    Prestige Whitworth Brogue - Black

    (86)

    $145.00 $125.00 Save $20.00

    Sale Prestige Whitworth Brogue

    Prestige Whitworth Brogue

    (187)

    $145.00 $125.00 Save $20.00

    Sale Prestige Bartlett Brogue - Tan

    Prestige Bartlett Brogue - Tan

    (143)

    $145.00 $125.00 Save $20.00

    Sale

    Any 2 for $160

    Classic Suede Oxford Shoe

    Classic Suede Oxford Shoe

    (79)

    $120.00 $95.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Oxford Shoe - Oxblood

    Classic Oxford Shoe - Oxblood

    (360)

    $120.00 $95.00 Save $25.00

    Sale Prestige Oxford Shoe - Rubber Sole

    Prestige Oxford Shoe - Rubber Sole

    (47)

    $145.00 $125.00 Save $20.00

    Sale

    Any 2 for $190

    Prestige Oxford Dress Shoe - Black

    Prestige Oxford Dress Shoe - Black

    (133)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $190

    Prestige Dress Shoe - Black

    Prestige Dress Shoe - Black

    (246)

    $140.00 $115.00 Save $25.00

    Sale Prestige Cumbria Boot

    Prestige Cumbria Boot

    (191)

    $145.00 $125.00 Save $20.00

    Sale

    Any 2 for $190

    Prestige Leather Lace-Up Deck Shoe

    Prestige Leather Lace-Up Deck Shoe

    (406)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $190

    Prestige Deck Shoe

    Prestige Deck Shoe

    (312)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $190

    Prestige Lace-Up Deck Shoe

    Prestige Lace-Up Deck Shoe

    (241)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Penny Loafer - Black Suede

    Classic Penny Loafer - Black Suede

    (79)

    $105.00 $95.00 Save $10.00

    Sale

    Any 2 for $190

    Prestige Twin Monk Shoe - Oxblood

    Prestige Twin Monk Shoe - Oxblood

    (144)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Slip-On Deck Shoe

    Classic Slip-On Deck Shoe

    (431)

    $120.00 $95.00 Save $25.00

    Sale

    Any 2 for $190

    Prestige Slip-On Deck Shoe - Brown

    Prestige Slip-On Deck Shoe - Brown

    (352)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $190

    Prestige Slip-On Boat Shoe

    Prestige Slip-On Boat Shoe

    (340)

    $140.00 $115.00 Save $25.00

    Sale Prestige Chelsea Boot - Black

    Prestige Chelsea Boot - Black

    (1486)

    $145.00 $125.00 Save $20.00

    Sale Prestige Chelsea Boot

    Prestige Chelsea Boot

    (346)

    $145.00 $125.00 Save $20.00

    Sale

    Any 2 for $190

    Prestige Oxford Shoe - Black

    Prestige Oxford Shoe - Black

    (807)

    $140.00 $115.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Semi-Brogue - Black

    Classic Semi-Brogue - Black

    (4135)

    $120.00 $95.00 Save $25.00

    Sale

    Any 2 for $160

    Classic Deck Shoe

    Classic Deck Shoe

    (750)

    $120.00 $95.00 Save $25.00

    Samuel Windsor

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