0871 911 7044*

My Account
End of season sale Save up to 70% on typical high street prices

30-day worn or unworn returns guarantee

Summer sale now on

Order Before 3pm
for same day despatch.

Find Your Size

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
















115,719

Independent customer reviews

Most Popular

  1. Classic Oxford Shoe
    £37.50

  2. Classic Penny Loafer Shoe
    £37.50

  3. Classic Cheltenham Brogue
    £37.50

  4. Classic Deck Shoe
    £35.00

  5. Classic Oxford Shoe
    £37.50

  6. Summer Weight Chino Trousers
    £20.00

  7. Suit Trousers
    £29.00

  8. Suit Trousers
    £29.00

  9. Short Sleeve Linen Shirt
    £15.00

  10. Classic Kempton Shoe
    £37.50

Prestige Tasselled Loafer - Black

SALE

Prestige Tasselled Loafer - Black

£47.50

Typical High Street Price: £132.67

Save £85.17

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

More Info
(490 reviews)
Prestige Tasselled Suede Loafer

SALE

Prestige Tasselled Suede Loafer

£47.50

Typical High Street Price: £132.67

Save £85.17

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

More Info
(242 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£37.50

Typical High Street Price: £132.67

Save £95.17

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

More Info
(281 reviews)
Prestige Penny Loafer - Black

SALE

Prestige Penny Loafer - Black

£47.50

Typical High Street Price: £132.67

Save £85.17

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

More Info
(220 reviews)
Prestige Penny Loafer

SALE

Prestige Penny Loafer

£47.50

Typical High Street Price: £132.67

Save £85.17

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

More Info
(179 reviews)
Prestige Tasselled Loafer

SALE

Prestige Tasselled Loafer

£47.50

Typical High Street Price: £132.67

Save £85.17

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

More Info
(40 reviews)
Prestige Penny Loafer Suede - Navy

SALE

Prestige Penny Loafer Suede - Navy

£47.50

Typical High Street Price: £132.67

Save £85.17

These suede Penny loafers will provide a fantastic complement to your summer casual wardrobe.

More Info
(44 reviews)
Prestige Penny Loafer Suede - Brown

SALE

Prestige Penny Loafer Suede - Brown

£47.50

Typical High Street Price: £132.67

Save £85.17

These suede Penny loafers will provide a fantastic complement to your summer casual wardrobe.

More Info
(1 reviews)
Prestige Penny Loafer Suede - Blue

SALE

Prestige Penny Loafer Suede - Blue

£47.50

Typical High Street Price: £132.67

Save £85.17

These suede Penny loafers will provide a fantastic complement to your summer casual wardrobe.

More Info
Classic Penny Loafer Shoe - Black

SALE

Classic Penny Loafer Shoe - Black

£37.50

Typical High Street Price: £132.67

Save £95.17

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

More Info
(3519 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£37.50

Typical High Street Price: £132.67

Save £95.17

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

More Info
(1815 reviews)
Classic Kempton Shoe - Black

SALE

Classic Kempton Shoe - Black

£37.50

Typical High Street Price: £132.67

Save £95.17

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

More Info
(1716 reviews)
Classic Kempton Shoe

SALE

Classic Kempton Shoe

£37.50

Typical High Street Price: £132.67

Save £95.17

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.

More Info
(2159 reviews)
Classic Penny Loafer

SALE

Classic Penny Loafer

£37.50

Typical High Street Price: £132.67

Save £95.17

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

More Info
(825 reviews)

Men's loafers are versatile and comfortable. Perfect for business and pleasure. Black penny loafers are sufficiently formal to wear with a suit, or for a bit of informal flair try a pair of brown suede loafers. If you want to know more about these legendary slip on shoes, read our loafers guide. Still not sure if loafers are for you? Check out our comprehensive collection of classic leather shoes for men.