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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 colours. 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 Boots Brogues Brown Shoes Chelsea Boots Chukka Boots Classic Shoes Crepe Sole Boots Deck Shoes Derby Shoes Formal Shoes Leather Slippers Lightweight Shoes Loafers Oxford Shoes Prestige Shoes Sandals Tan Shoes Trainers Read More
    Refine By
    Sale

    Any 2 for £30

    Grecian Slipper - Black

    Grecian Slipper - Black

    (207)

    £37.50 £17.50 Save £20.00

    Comparable High Street Price: £28.17

    Sale

    Any 2 Pairs for £45 or 3 for £60

    Prestige Deck Shoe - Tan

    Prestige Deck Shoe - Tan

    (410)

    £32.50 £25.00 Save £7.50

    Comparable High Street Price: £116.25

    Sale Prestige Davington Brogue - Tan

    Prestige Davington Brogue - Tan

    (27)

    £39.95 £27.50 Save £12.45

    Comparable High Street Price: £144.74

    Sale Prestige Semi-Brogue

    Prestige Semi-Brogue

    (592)

    £49.95

    Comparable High Street Price: £96.75

    Sale

    Any 2 Pairs for £40 or 3 for £50

    Classic Moccasin

    Classic Moccasin

    (119)

    £27.50 £22.50 Save £5.00

    Comparable High Street Price: £83.75

    Sale Prestige Chiltern Boot - Brown

    Prestige Chiltern Boot - Brown

    (47)

    £59.00 £29.95 Save £29.05

    Comparable High Street Price: £138.49

    Sale

    Any 2 Pairs for £40 or 3 for £50

    Classic Deck Shoe - Tobacco

    Classic Deck Shoe - Tobacco

    (46)

    £27.50 £22.50 Save £5.00

    Comparable High Street Price: £83.25

    Sale Prestige Chukka Boots - Tan

    Prestige Chukka Boots - Tan

    (33)

    £65.00 £39.00 Save £26.00

    Comparable High Street Price: £176.00

    Sale Prestige Bartlett Brogue In Tweed

    Prestige Bartlett Brogue In Tweed

    (46)

    £65.00 £35.00 Save £30.00

    Comparable High Street Price: £144.74

    Sale

    Any 2 Pairs for £40 or 3 for £50

    Classic Leather Driving Shoe

    Classic Leather Driving Shoe

    (86)

    £27.50 £22.50 Save £5.00

    Comparable High Street Price: £83.75

    Sale

    Any 2 for £30

    Outdoor Mule – Burgundy

    Outdoor Mule – Burgundy

    (10)

    £42.50 £17.50 Save £25.00

    Comparable High Street Price: £59.67

    Sale

    Any 2 Pairs for £40 or 3 for £50

    Classic Oxford Shoe

    Classic Oxford Shoe

    (400)

    £27.50 £22.50 Save £5.00

    Comparable High Street Price: £144.74

    Sale Prestige Chiltern Boot - Nubuck

    Prestige Chiltern Boot - Nubuck

    (13)

    £59.00 £29.95 Save £29.05

    Comparable High Street Price: £138.49

    Sale Prestige Cumbria Boot

    Prestige Cumbria Boot

    (191)

    £59.00 £29.00 Save £30.00

    Comparable High Street Price: £138.49

    Sale Prestige Penny Loafer - Black

    Prestige Penny Loafer - Black

    (322)

    £49.95 £22.50 Save £27.45

    Comparable High Street Price: £143.50

    Sale

    Any 2 Pairs for £45 or 3 for £60

    Prestige Suede Trainers - Grey

    Prestige Suede Trainers - Grey

    (7)

    £39.95 £25.00 Save £14.95

    Comparable High Street Price: £86.25

    Sale Prestige Country Boot In Tweed

    Prestige Country Boot In Tweed

    (42)

    £75.00 £39.00 Save £36.00

    Comparable High Street Price: £144.74

    Sale

    Any 2 Pairs for £40 or 3 for £50

    Classic Driving Shoe

    Classic Driving Shoe

    (110)

    £27.50 £22.50 Save £5.00

    Comparable High Street Price: £83.75

    Sale Prestige Penny Loafer

    Prestige Penny Loafer

    (266)

    £49.95 £25.00 Save £24.95

    Comparable High Street Price: £143.50

    Sale Prestige Driving Shoe - Navy/Brown

    Prestige Driving Shoe - Navy/Brown

    (46)

    £49.95 £25.00 Save £24.95

    Comparable High Street Price: £83.75

    Sale

    Any 2 Pairs for £45 or 3 for £60

    Prestige Deck Shoe - Navy

    Prestige Deck Shoe - Navy

    (353)

    £32.50 £25.00 Save £7.50

    Comparable High Street Price: £116.25

    Sale

    Any 2 Pairs for £45 or 3 for £60

    Prestige Deck Shoe - Grey

    Prestige Deck Shoe - Grey

    (410)

    £32.50 £25.00 Save £7.50

    Comparable High Street Price: £116.25

    Sale Prestige Crepe Sole Desert Boots - Tan

    Prestige Crepe Sole Desert Boots - Tan

    (3)

    £59.00 £25.00 Save £34.00

    Comparable High Street Price: £65.50

    Sale Prestige Suede Chelsea Boot - Black

    Prestige Suede Chelsea Boot - Black

    (27)

    £55.00

    Comparable High Street Price: £176.00

    Sale

    Any 2 Pairs for £40 or 3 for £50

    Classic Derby Shoe - Suede

    Classic Derby Shoe - Suede

    (12)

    £27.50 £22.50 Save £5.00

    Comparable High Street Price: £138.25

    Sale

    Any 2 Pairs for £45 or 3 for £60

    Prestige Penny Loafer - Tan

    Prestige Penny Loafer - Tan

    (266)

    £32.50 £25.00 Save £7.50

    Comparable High Street Price: £143.50

    Sale Prestige Monk Boot - Black

    Prestige Monk Boot - Black

    (34)

    £49.95

    Comparable High Street Price: £138.49

    Sale Prestige Penny Loafer - Suede - Black

    Prestige Penny Loafer - Suede - Black

    (29)

    £49.95 £27.50 Save £22.45

    Comparable High Street Price: £143.50

    Sale Prestige Chukka Boot - Suede

    Prestige Chukka Boot - Suede

    (16)

    £65.00 £25.00 Save £40.00

    Comparable High Street Price: £176.00

    Sale Prestige Whitworth Brogue - Tan

    Prestige Whitworth Brogue - Tan

    (187)

    £55.00 £25.00 Save £30.00

    Comparable High Street Price: £158.32

    Sale

    Any 2 Pairs for £40 or 3 for £50

    Classic Derby Shoe - Black Suede

    Classic Derby Shoe - Black Suede

    (19)

    £27.50 £22.50 Save £5.00

    Comparable High Street Price: £138.25

    Sale Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (39)

    £49.95 £25.00 Save £24.95

    Comparable High Street Price: £73.49

    Sale Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (39)

    £49.95 £25.00 Save £24.95

    Comparable High Street Price: £73.49

    Sale

    Any 2 Pairs for £45 or 3 for £60

    Prestige Suede Trainers - Tan

    Prestige Suede Trainers - Tan

    (8)

    £39.95 £25.00 Save £14.95

    Comparable High Street Price: £86.25

    Sale Prestige Lightweight Derby - Navy Suede

    Prestige Lightweight Derby - Navy Suede

    (39)

    £49.95 £25.00 Save £24.95

    Comparable High Street Price: £73.49

    Sale

    Any 2 Pairs for £45 or 3 for £60

    Prestige Penny Loafer - Black

    Prestige Penny Loafer - Black

    (322)

    £32.50 £25.00 Save £7.50

    Comparable High Street Price: £143.50

    Sale Prestige Lightweight Derby - Tobacco

    Prestige Lightweight Derby - Tobacco

    (41)

    £49.95 £25.00 Save £24.95

    Comparable High Street Price: £73.49

    Sale Prestige Oxford Shoe - Rubber Sole

    Prestige Oxford Shoe - Rubber Sole

    (47)

    £52.95 £25.00 Save £27.95

    Comparable High Street Price: £144.74

    Sale Prestige Davington Brogue - Black

    Prestige Davington Brogue - Black

    (22)

    £45.00

    Comparable High Street Price: £144.74

    Sale Prestige Crepe Sole Chelsea Boots - Tan

    Prestige Crepe Sole Chelsea Boots - Tan

    (4)

    £59.00 £25.00 Save £34.00

    Comparable High Street Price: £65.50

    Sale Prestige Crepe Sole Desert Boots - Grey

    Prestige Crepe Sole Desert Boots - Grey

    (2)

    £59.00 £25.00 Save £34.00

    Comparable High Street Price: £65.50

    Sale Prestige Crepe Sole Desert Boots - Navy

    Prestige Crepe Sole Desert Boots - Navy

    (4)

    £59.00 £25.00 Save £34.00

    Comparable High Street Price: £65.50

    Sale

    Any 2 for £30

    Leather Soled Sandal - Black

    Leather Soled Sandal - Black

    (0)

    £32.50 £17.50 Save £15.00

    Sale

    Any 2 for £30

    Leather Soled Sandal - Tan

    Leather Soled Sandal - Tan

    (1)

    £32.50 £17.50 Save £15.00

    Sale Prestige Crepe Sole Chelsea Boots - Navy

    Prestige Crepe Sole Chelsea Boots - Navy

    (0)

    £59.00 £25.00 Save £34.00

    Comparable High Street Price: £65.50

    Sale Prestige Tweed Brogue - Exmoor

    Prestige Tweed Brogue - Exmoor

    (7)

    £32.50

    Comparable High Street Price: £144.74

    Sale

    Any 2 for £30

    Churchill Suede Moccasin Slipper

    Churchill Suede Moccasin Slipper

    (280)

    £35.00 £17.50 Save £17.50

    Sale

    Any 2 for £30

    Churchill Suede Moccasin

    Churchill Suede Moccasin

    (576)

    £35.00 £17.50 Save £17.50

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