BROGUES | CLASSIC | CHELTENHAM | MONK | PENNY LOAFER | HENLEY | KEMPTON | OXFORD | RICHMOND | CASUAL

Penny Loafers are lace-less, low cut shoe. The most commonly seen style is known as a loafer in America, it has a moccasin construction. First appearing in the mid-1930s from Norway, they began as casual shoes and have increased in popularity to point of that they are now worn with suits, though lace-up shoes are stil required in more conservative locations like the UK. They are available in a wide variety of different colours and designs, often with tassels, or metal decorations on the front.

Below is a selection of leather Monk shoes hand crafted to the highest standard

Penny Loafer Men's Real Leather Shoes  Penny Loafer Men's Real Leather Shoes

These Penny Loafers are men's genuine leather shoes featuring real leather uppers. A traditional casual with a classic feel, these Penny Loafer genuine leather shoes feature soles that are hand-stitched AND glued - a unique feature not found in other shoes at this great price. Take advantage now of this unique offer whilst stocks last! Available in Black (LFK) or Brown (LFR). Sizes: Mens Sizes: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13 ...

From £34.99
Tell me more about Penny Loafer Men's Real Leather Shoes


Prestige Penny Loafer - Brown - Italian Leather Upper  Prestige Penny Loafer - Brown - Italian Leather Upper

With uppers made from the finest Italian leather, these brown Prestige Penny Loafer shoes from Samuel Windsor are beautifully styled and supremely comfortable. Fantastic comfort and wearability, these Penny loafer shoes are built to last and keep their good looks for years to come. Classically styled and perfect for a busy lifestyle, these will function equally as well as formal shoes or with casual wear. Features of the Prestige Penny Loafer Shoe: Italian Leather Upper for incredible comfort and durability. Classic Penny Loafer styling with easy slip-on access Available from size 5 to size 14, including half-sizes. Built to wear beautifully for years. Sizes Available: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13, 14. Please note this shoe has a combined leather/rubber sole. Provided with a shoe horn. Code: BVH14 Please Note: This shoe features a combined leather/rubber sole. ...

From £49.95
Tell me more about Prestige Penny Loafer - Brown - Italian Leather Upper


Classic Penny Loafer Shoe - Chestnut Brown  Classic Penny Loafer Shoe - Chestnut Brown

These handmade Penny Loafer men's leather shoes are classic formal shoes combined with supple easy slip on access. The handmade Penny Loafer men's leather shoes accommodating leather upper has been handcrafted, raising it to the highest level of shoe quality. The Goodyear Welted sole delivers hard wearing comfort that meets the needs of any busy lifestyle. Provided with a shoehorn. Colour: Chestnut Brown (BV41) Sizes: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13, 14 ...

From £39.95
Tell me more about Classic Penny Loafer Shoe - Chestnut Brown


Classic Penny Loafer Handmade Shoe: Chestnut Brown  Classic Penny Loafer Handmade Shoe: Chestnut Brown

This Penny Loafer slip-on shoe, in black, is classically formal with easy slip-on access. Handmade with an accomodating leather upper, these shoes are at the pinnacle of shoe quality and designed to meet the challenges of a busy lifestyle. Provided with a shoehorn. Colour: Chestnut Brown (BV41) ...

From £39.95
Tell me more about Classic Penny Loafer Handmade Shoe: Chestnut Brown


Prestige Penny Loafer - Black - Italian Leather Upper  Prestige Penny Loafer - Black - Italian Leather Upper

The black Penny Loafer shoes from Samuel Windsor's Prestige range feature classic loafer styling with supple easy slip-on access. Handmade, featuring uppers crafted from the finest Italian leather, these shoes are built to last and designed to wear beautifully day after day. Great as a pair of office shoes, they also work well with more formal attire or even with a smart casual look. Produced by Samuel Windsor craftsmen, these are perfect shoes for gentlemen with a busy lifestyle who need a pair of comfortable, durable and good looking shoes. Features of the Prestige Penny Loafer Shoe: Italian Leather Upper. Classic Penny Loafer styling for great looks. Available from size 5 to size 14, including half-sizes. Built to wear beautifully for years. Provided with a shoe horn. Sizes Available: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13, 14. Code: BVH13 Please Note: This shoe features a combined leather/rubber sole. ...

From £49.95
Tell me more about Prestige Penny Loafer - Black - Italian Leather Upper


Classic Penny Loafer Suede  Classic Penny Loafer Suede

Owning a pair of Samuel Windsor handmade leather shoes is a once in a lifetime expereince. This Penny Loafer Suede offers the unique combination of unrivalled comfort and rugged wearability which is the hallmark of the genuinely crafted handmade shoes. Our Classic collection are perfect for the genuinely smart man, and which look equally at home with a formal suit for work or with weekend casual attire. Provided with a shoehorn. Available in Sizes: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13, 14 CODE: BV114 ...

From £49.95
Tell me more about Classic Penny Loafer Suede


Classic Penny Loafer Handmade Shoe: Black  Classic Penny Loafer Handmade Shoe: Black

This Penny Loafer slip-on shoe, in black, is classically formal with easy slip-on access. Handmade with an accomodating leather upper, these shoes are at the pinnacle of shoe quality and designed to meet the challenges of a busy lifestyle. Provided with a shoehorn. Colour: Black (BV36) Click here to view this Penny Loafers in Chestnut Brown Sizes: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13, 14 ...

From £39.95
Tell me more about Classic Penny Loafer Handmade Shoe: Black


Prestige Penny Loafer - Brown - Italian Leather Upper  Prestige Penny Loafer - Brown - Italian Leather Upper

With uppers made from the finest Italian leather, these brown Prestige Penny Loafer shoes from Samuel Windsor are beautifully styled and supremely comfortable. Fantastic comfort and wearability, these Penny loafer shoes are built to last and keep their good looks for years to come. Classically styled and perfect for a busy lifestyle, these will function equally as well as formal shoes or with casual wear. Features of the Prestige Penny Loafer Shoe: Goodyear Welted Construction for long lasting wear. Italian Leather Upper for incredible comfort and durability. Classic Penny Loafer styling with easy slip-on access Available from size 5 to size 14, including half-sizes. Built to wear beautifully for years. Provided with a shoehorn. Sizes Available: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13, 14. Please note this shoe has a combined leather/rubber sole. Code: BVH14 ...

From £49.95
Tell me more about Prestige Penny Loafer - Brown - Italian Leather Upper


Classic Penny Loafer Shoe - Black  Classic Penny Loafer Shoe - Black

This handmade Penny Loafer Shoe is a classic dress style combined with supple easy slip on access. The handmade Penny Loafer Shoe's accommodating leather upper has been handcrafted, raising it to the highest level of shoe quality. The Goodyear Welted sole delivers hard wearing comfort that meets the needs of any busy lifestyle. Provided with a shoehorn. Penny Loafer Colour: Black (BV36) Penny Loafer Sizes: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13, 14 ...

From £39.95
Tell me more about Classic Penny Loafer Shoe - Black


Classic Penny Loafer Suede  Classic Penny Loafer Suede

Owning a pair of Samuel Windsor handmade leather shoes is a once in a lifetime expereince. This Penny Loafer Suede offers the unique combination of unrivalled comfort and rugged wearability which is the hallmark of the genuinely crafted handmade shoes. Our Classic collection are perfect for the genuinely smart man, and which look equally at home with a formal suit for work or with weekend casual attire. Provided with a shoehorn. Available in Sizes: 5, 6, 6½, 7, 7½, 8, 8½, 9, 9½, 10, 11, 12, 13, 14 CODE: BV114 ...

From £49.95
Tell me more about Classic Penny Loafer Suede