Basket (0) My Account

0871 911 7044*

30-day worn or unworn returns guarantee

You Are Here: Home >

Summer sale - Save up to 75‰

Sameday despatch?
Place your order in:

::Hours Mins Secs

Find Your Size

Select your size to show products in this category with your size in stock.
















Feefo Reviews

Customers independently
rate our excellent service

95%
104,029 Reviews

Most Popular

  1. Classic Oxford Shoe
    £35.00

  2. Classic Penny Loafer Shoe
    £35.00

  3. Classic Cheltenham Brogue
    £35.00

  4. Outdoor Mule
    £30.00

  5. Classic Deck Shoe
    £32.50

  6. Classic Oxford Shoe
    £35.00

  7. Classic Sandhurst Shoe
    £35.00

  8. Classic Kempton Shoe
    £35.00

  9. Classic Quarter-Brogue
    £35.00

  10. Classic Monk Shoe
    £35.00

Mens ShoesFROM £25.00

Classic Driving Shoe

SALE

Classic Driving Shoe

£32.50

Typical High Street Price: £62.50

Classic Driving Shoe are comfortable to wear which is perfect for the summer.

Save £30.00

More Info
91% (70 reviews)
Classic Moccasin

SALE

Classic Moccasin

£32.50

Typical High Street Price: £62.50

Made from the finest, soft Italian leather, our Classic moccasins are carefully hand stitched, creating a wonderfully comfortable and durable casual shoe.

Save £30.00

More Info
100% (58 reviews)
Prestige Brogue

SALE

Prestige Brogue

£45.00

Typical High Street Price: £134.75

Prestige Brown Brogues, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
91% (22 reviews)
Prestige Oxford

SALE

Prestige Oxford

£45.00

Typical High Street Price: £124.75

Prestige Oxford Shoe, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £79.75

More Info
92% (51 reviews)
Prestige Split Brogue

SALE

Prestige Split Brogue

£45.00

Typical High Street Price: £134.75

Prestige Split Brogue, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
100% (40 reviews)
Prestige Twin Monk

SALE

Prestige Twin Monk

£45.00

Typical High Street Price: £131.00

Prestige Twin Monk, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £86.00

More Info
81% (31 reviews)
Prestige Brogue

SALE

Prestige Brogue

£45.00

Typical High Street Price: £134.75

Prestige Black Brogues, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
96% (50 reviews)
Prestige Lightweight Brogue

SALE

Prestige Lightweight Brogue

£45.00

Typical High Street Price: £134.75

Prestige Suede Brogues, online from Samuel Windsor. Visit us now for exceptional quality at outstanding prices.

Save £89.75

More Info
100% (14 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50

Typical High Street Price: £88.50

Classic Deck Shoe from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

Save £56.00

More Info
100% (43 reviews)
Nubuck Trainer - Earth Sole

SALE

Nubuck Trainer - Earth Sole

£25.00

Nubuck Trainer - Earth Sole, online from Samuel Windsor. Tailored quality at outstanding prices.

More Info
95% (40 reviews)
Casual lace-up

SALE

Casual lace-up

£25.00

Casual Lace Up shoes, online from Samuel Windsor. Tailored quality at outstanding prices.

More Info
95% (19 reviews)
Prestige Tasselled Loafer

SALE

Prestige Tasselled Loafer

£45.00

Typical High Street Price: £127.67

Prestige Tasselled Loafer - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £82.67

More Info
89% (19 reviews)
Prestige Deck Shoe

SALE

Prestige Deck Shoe

£45.00

Typical High Street Price: £109.74

These Prestige deck shoes are supremely comfortable, fabulously affordable and crafted using Italian leather. Visit now for great offers.

Save £64.74

More Info
96% (47 reviews)
Prestige Gibson Shoe

SALE

Prestige Gibson Shoe

£45.00

Typical High Street Price: £106.17

These Goodyear Welted, Prestige Gibson shoes, featuring Italian grained leather uppers, as well as a practical rubber sole, they have country styling, and are ideal as a more subtle choice of quality men’s shoe.

Save £61.17

More Info
93% (28 reviews)
Prestige Dress Shoe

SALE

Prestige Dress Shoe

£45.00

Typical High Street Price: £85.75

Finish off that formal outfit with a pair of men’s dress shoes from our Prestige range.

Save £40.75

More Info
96% (104 reviews)
Prestige Country Boot - Rubber Sole

SALE

Prestige Country Boot - Rubber Sole

£35.00

Typical High Street Price: £134.33

Prestige Country Boot - Antique Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.33

More Info
99% (117 reviews)
Prestige Country Boot - Rubber Sole

SALE

Prestige Country Boot - Rubber Sole

£35.00

Typical High Street Price: £134.33

Prestige Country Boot, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.33

More Info
100% (91 reviews)
Classic Oxford Shoe - Cigar

SALE

Classic Oxford Shoe - Cigar

£35.00

Typical High Street Price: £124.75

Classic Oxford Shoes - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
94% (126 reviews)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£35.00

Typical High Street Price: £134.75

Classic Semi-Brogues - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
99% (73 reviews)
Classic Quarter-Brogue

SALE

Classic Quarter-Brogue

£35.00

Typical High Street Price: £134.75

Classic Quarter-Brogues - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
94% (54 reviews)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£35.00

Typical High Street Price: £134.75

Classic Sandhurst Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
98% (54 reviews)
Prestige Oxford Shoe

SALE

Prestige Oxford Shoe

£45.00

Typical High Street Price: £124.75

Featuring a classic Oxford shoe design, these Goodyear Welted men’s shoes offer all the luxury you could ask for.

Save £79.75

More Info
97% (30 reviews)
Prestige Belgravia Shoe

SALE

Prestige Belgravia Shoe

£45.00

These nubuck men’s boots are a great addition to any gent’s wardrobe.

More Info
97% (65 reviews)
Prestige Deck Boot

SALE

Prestige Deck Boot

£45.00

Typical High Street Price: £109.74

Sturdy design meets the styling of a deck shoe in this Prestige Deck Boot.

Save £64.74

More Info
100% (29 reviews)
Prestige Country Oxford Shoe

SALE

Prestige Country Oxford Shoe

£35.00

Typical High Street Price: £106.17

Country style meets classic men’s shoe design in this Prestige Country Oxford Shoe from the Samuel Windsor Prestige range.

Save £71.17

More Info
97% (67 reviews)
Prestige Chelsea Boot

SALE

Prestige Chelsea Boot

£45.00

Typical High Street Price: £144.50

Prestige Chelsea Boot, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.50

More Info
93% (129 reviews)
Classic Quarter-Brogue - Black

SALE

Classic Quarter-Brogue - Black

£35.00

Typical High Street Price: £134.75

Classic Plain Toe Cap Quarter Brogue - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
98% (163 reviews)
Prestige Kensington Boot - Rubber Sole

SALE

Prestige Kensington Boot - Rubber Sole

£35.00

Typical High Street Price: £134.33

Prestige Kensington Boot - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.33

More Info
98% (48 reviews)
Prestige Lightweight Derby Shoe

SALE

Prestige Lightweight Derby Shoe

£45.00

Prestige Lightweight Derby Shoe - Sand Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

More Info
98% (48 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£35.00

Typical High Street Price: £88.50

Classic Deck Shoe - Blue/Brown/White, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £53.50

More Info
80% (152 reviews)
Classic Durham Shoe

SALE

Classic Durham Shoe

£35.00

Typical High Street Price: £134.75

Classic Durham Shoe - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
89% (61 reviews)
Prestige Penny Loafer - Black

SALE

Prestige Penny Loafer - Black

£45.00

Typical High Street Price: £127.67

Prestige Penny Loafer - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £82.67

More Info
92% (77 reviews)
Prestige Penny Loafer

SALE

Prestige Penny Loafer

£45.00

Typical High Street Price: £127.67

Prestige Penny Loafer - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £82.67

More Info
93% (55 reviews)
Prestige Monk Shoe - Rubber Sole - Black

SALE

Prestige Monk Shoe - Rubber Sole - Black

£35.00

Typical High Street Price: £131.00

Prestige Monk Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £96.00

More Info
93% (75 reviews)
Prestige Gibson Shoe - Rubber Sole

SALE

Prestige Gibson Shoe - Rubber Sole

£45.00

Typical High Street Price: £106.17

Prestige Gibson Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £61.17

More Info
92% (49 reviews)
Prestige Kensington Boot - Rubber Sole - Black

SALE

Prestige Kensington Boot - Rubber Sole - Black

£45.00

Typical High Street Price: £134.33

Prestige Kensington Boot - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.33

More Info
91% (47 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50

Typical High Street Price: £88.50

Classic Deck Shoe in Navy from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

Save £56.00

More Info
99% (87 reviews)
Prestige Derby Shoe

SALE

Prestige Derby Shoe

£45.00

Typical High Street Price: £127.00

Prestige Derby Shoe - Navy Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £82.00

More Info
97% (79 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£35.00

Typical High Street Price: £124.75

Classic Oxford Shoes - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
98% (132 reviews)
Prestige Dealer Boot - Rubber Sole

SALE

Prestige Dealer Boot - Rubber Sole

£35.00

Typical High Street Price: £134.33

Prestige Dealer Boot - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.33

More Info
88% (56 reviews)
Prestige Dealer Boot - Rubber Sole

SALE

Prestige Dealer Boot - Rubber Sole

£35.00

Typical High Street Price: £134.33

Prestige Dealer Boot - Tobacco, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.33

More Info
92% (49 reviews)
Prestige Slip-On Deck Shoe

SALE

Prestige Slip-On Deck Shoe

£45.00

Typical High Street Price: £109.74

Prestige Leather Slip-On Boat Shoe - made with the finest Italian leather uppers or a luxury finish and unbeatable comfort and durability.

Save £64.74

More Info
91% (103 reviews)
Prestige Slip-On Deck Shoe

SALE

Prestige Slip-On Deck Shoe

£45.00

Typical High Street Price: £109.74

Our Prestige Slip-on Boat Shoes with contrasting colours is the epitome of casual sophistication. Visit us now for great offers on leather deck shoes.

Save £64.74

More Info
94% (109 reviews)
Classic Lace-Up Deck Shoe

SALE

Classic Lace-Up Deck Shoe

£32.50

Typical High Street Price: £88.50

Our Classic Lace-Up Boat Shoes are handmade by Samuel Windsor. These designer lace-up shoes are crafted using only the finest leathers.

Save £56.00

More Info
91% (34 reviews)
Prestige Cumbria Boot

SALE

Prestige Cumbria Boot

£45.00

Prestige Cumbria Boot - Mid Brown, a lace-up shoe with an exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

More Info
97% (63 reviews)
Prestige Lace-Up Deck Shoe

SALE

Prestige Lace-Up Deck Shoe

£45.00

Typical High Street Price: £109.74

Prestige Leather Lace-Up Boat Shoe - exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

Save £64.74

More Info
95% (144 reviews)
Prestige Lace-Up Deck Shoe

SALE

Prestige Lace-Up Deck Shoe

£45.00

Typical High Street Price: £109.74

Our Prestige Lace-Up Boat Shoes with contrasting colours is the epitome of casual sophistication. Visit us now for great offers on leather deck shoes.

Save £64.74

More Info
88% (50 reviews)
Prestige Lightweight Brogue

SALE

Prestige Lightweight Brogue

£45.00

Typical High Street Price: £134.75

Prestige Lightweight Brogue - Tobacco, a brogue shoe with an exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

Save £89.75

More Info
97% (104 reviews)
Prestige Chelsea Boot - Black

SALE

Prestige Chelsea Boot - Black

£45.00

Typical High Street Price: £144.50

Prestige Chelsea Boots: Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.50

More Info
97% (187 reviews)
Prestige Suede Chelsea Boot

SALE

Prestige Suede Chelsea Boot

£45.00

Typical High Street Price: £144.50

Prestige Chelsea Boots: Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.50

More Info
95% (103 reviews)
Prestige Leather/Canvas Brogue

SALE

Prestige Leather/Canvas Brogue

£45.00

Typical High Street Price: £134.75

Leather and canvas brogues from our Prestige range are the pinnacle of versatility. Choose from a range of colours at Samuel Windsor online.

Save £89.75

More Info
90% (30 reviews)
Prestige Leather/Canvas Brogue

SALE

Prestige Leather/Canvas Brogue

£45.00

Typical High Street Price: £134.75

Prestige Leather/Canvas Brogue from our Prestige range are the pinnacle of versatility.

Save £89.75

More Info
96% (52 reviews)
Classic Semi-Brogue - Black

SALE

Classic Semi-Brogue - Black

£35.00

Typical High Street Price: £134.75

Classic Semi-Brogues - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
97% (228 reviews)
Classic Semi-Brogue

SALE

Classic Semi-Brogue

£35.00

Typical High Street Price: £134.75

Classic Suede Semi-Brogues - Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
98% (133 reviews)
Classic Monk Shoe - Black

SALE

Classic Monk Shoe - Black

£35.00

Typical High Street Price: £131.00

These handmade Monk Shoes is another traditional classic from Samuel Windsor, painstakingly constructed from over 50 natural components. The monk strap leather design is powerful in appearance.

Save £96.00

More Info
96% (262 reviews)
Classic Monk Shoe

SALE

Classic Monk Shoe

£35.00

Typical High Street Price: £131.00

Classic Monk Shoes - Chestnut Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £96.00

More Info
96% (182 reviews)
Prestige Tasselled Loafer - Black

SALE

Prestige Tasselled Loafer - Black

£45.00

Typical High Street Price: £127.67

Prestige Tasselled Loafer - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £82.67

More Info
94% (83 reviews)
Prestige Brogue - Rubber Sole - Black

SALE

Prestige Brogue - Rubber Sole - Black

£45.00

Typical High Street Price: £134.75

Prestige Brogue: Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
96% (80 reviews)
Prestige Brogue - Rubber Sole

SALE

Prestige Brogue - Rubber Sole

£45.00

Typical High Street Price: £134.75

Prestige Brogue: Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
95% (84 reviews)
Classic Sandhurst Shoe

SALE

Classic Sandhurst Shoe

£35.00

Typical High Street Price: £134.75

Classic Sandhurst Shoe - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
94% (224 reviews)
Classic Sandhurst Shoe - Black

SALE

Classic Sandhurst Shoe - Black

£35.00

Typical High Street Price: £134.75

Classic Sandhurst Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £99.75

More Info
94% (113 reviews)
Prestige Tasselled Suede Loafer

SALE

Prestige Tasselled Suede Loafer

£45.00

Typical High Street Price: £127.67

Prestige Tasselled Loafer - Blue Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £82.67

More Info
91% (67 reviews)
Prestige Country Brogue - Rubber Sole

SALE

Prestige Country Brogue - Rubber Sole

£45.00

Typical High Street Price: £134.75

Prestige Country Brogue - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
100% (48 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £127.67

Classic Penny Loafer - Dark Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £92.67

More Info
87% (109 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£32.50

Typical High Street Price: £88.50

Classic Deck Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £56.00

More Info
96% (147 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £127.67

Classic Penny Loafer Shoe - Chestnut Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £92.67

More Info
92% (226 reviews)
Classic Oxford Shoe

SALE

Classic Oxford Shoe

£35.00

Typical High Street Price: £124.75

Crafted using time honoured shoe making techniques, these Samuel Windsor Classic Oxford Shoes in chestnut brown are classic formal shoes or office shoes.

Save £89.75

More Info
95% (274 reviews)
Classic City Shoe - Black

SALE

Classic City Shoe - Black

£35.00

Typical High Street Price: £127.00

Classic City Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £92.00

More Info
93% (126 reviews)
Prestige Oxford Shoe - Rubber Sole - Black

SALE

Prestige Oxford Shoe - Rubber Sole - Black

£45.00

Typical High Street Price: £106.17

Black Oxford Shoes Rubber Sole, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £61.17

More Info
96% (137 reviews)
Classic Richmond Shoe - Black

SALE

Classic Richmond Shoe - Black

£35.00

Typical High Street Price: £127.00

Great office shoes, these Samuel Windsor Richmond Classics mens black shoes are handmade, incorporating a leather lining which is both breathable and seamless.

Save £92.00

More Info
89% (104 reviews)
Classic Cheltenham Brogue - Black

SALE

Classic Cheltenham Brogue - Black

£35.00

Typical High Street Price: £134.75

Cheltenham Half Brogues mens leather shoes, formal shoes or office shoes, mens brogue shoes which retain the elegant craftmanship personified by hand-stitching.

Save £99.75

More Info
95% (546 reviews)
Classic Kempton Shoe - Black

SALE

Classic Kempton Shoe - Black

£35.00

Typical High Street Price: £127.67

Classic Kempton Black Shoe - Slip-On, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £92.67

More Info
95% (215 reviews)
Classic Kempton Shoe

SALE

Classic Kempton Shoe

£35.00

Typical High Street Price: £127.67

Designed to look good with formal or casual wear, these Samuel Windsor real leather Kempton men's leather shoes, men's brown shoes, are an essential addition to any gentleman's wardrobe.

Save £92.67

More Info
97% (392 reviews)
Prestige Oxford Shoe - Black

SALE

Prestige Oxford Shoe - Black

£45.00

Typical High Street Price: £124.75

Prestige Oxford Black Shoe - Italian Leather Upper, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £79.75

More Info
91% (94 reviews)
Prestige Semi-Brogue - Black

SALE

Prestige Semi-Brogue - Black

£45.00

Typical High Street Price: £134.75

Prestige Semi-Brogue - Black - Italian Leather Upper, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
93% (73 reviews)
Prestige Semi-Brogue

SALE

Prestige Semi-Brogue

£45.00

Typical High Street Price: £134.75

Prestige Semi-Brogue - Tan - Italian Leather Upper, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £89.75

More Info
94% (34 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£35.00

Typical High Street Price: £127.67

Classic Penny Loafer Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

Save £92.67

More Info
94% (124 reviews)
Classic Oxford Shoe - Black

SALE

Classic Oxford Shoe - Black

£35.00

Typical High Street Price: £124.75

The Samuel Windsor commitment to quality ensures these handmade Classic black Oxford shoes will prove to be the finest, most comfortable and hardest wearing men's leather shoes you will ever invest in.

Save £89.75

More Info
96% (959 reviews)
Classic Penny Loafer Shoe - Black

SALE

Classic Penny Loafer Shoe - Black

£35.00

Typical High Street Price: £127.67

These black Penny Loafer men's leather shoes from Samuel Windsor are classic formal shoes combined with supple, easy slip-on access.

Save £92.67

More Info
93% (505 reviews)