From traditional classic footwear styles to casual modern styles, shop expertly crafted and designed shoes, from a handful of hand-selected brands. For the true gentleman, choose truly timeless shoes that don’t just sit on your feet, choose traditional shoemaking techniques, sturdy yet beautiful leathers and above all quality that stands the test of time. Discover your classic style with a truly fine pair of shoes. Because the true gentleman style never goes out of fashion. 


Our Range of Men’s Classic Shoes

Our collection of men’s classic shoes comprises high-quality dress shoes, suave loafers, casual boots and suit shoes to complement and complete your style. We proudly stock something for every occasion including British-made shoes, Goodyear welted shoes, stylish Chelsea boots, easy slip-on loafers and Weejuns to help you make your statement whatever the attire. Using only the highest quality leathers, the classic shoes we stock are built to last, and selected for their style, durability and comfort making up our fine range of classic shoes for men.


This quintessential dress shoe features a closed lacing system and a sleek, formal silhouette. Oxford shoes are perfect for business meetings, weddings, and other formal occasions.


Similar to Oxfords, Derbys have an open lacing system, for a slightly less formal aesthetic. A truly versatile option to be dressed up or down. Suitable for work, and weekend wear, including smart casual styles, seamlessly transitioning your outfit from work to play.


Our slip-on style Loafers come in a variety of styles and leathers, from the penny loafer with its signature strap across the vamp to the fun tassel loafer with decorative tassels. Both comfortable and stylish, a great option for casual wear or, dressed up for those slightly more formal occasions.

Chelsea Boots 

The classic ankle-high Chelsea boot with its signature elastic side panels makes Chelsea boots easy to slip on and off. Both a stylish and versatile options, to wear with jeans, chinos, or suits.

Chukka Boots 

The Chukka boot style consists of ankle-high boots with an open lacing system, typical of two or three pairs of eyelets, simple, fun and easy to style. One of our more casual boot options, easily worn with jeans or chinos - a little less formal than the Chelsea boot.

Shop Classic Shoes for Men with A Fine Pair of Shoes

Shop classic shoes for men from A Fine Pair of Shoes today for free 28-hour shipping over £40 and the flexibility of an extended returns period of 45 days, if you happen to change your mind easily return your shoes with our hassle-free returns. We want you to find the perfect pair of shoes so we’ve made sure our returns policy is as generous as it possibly could be. Choose from hundreds of shoes and a whole array of fine-quality brands hand-selected for their craftsmanship, sustainability and timeless designs. With truly classic, original designs and brands steeped in shoemaking history, choose quality, tradition and a truly fine pair of shoes. 


What factors should I consider when choosing a pair of classic men’s shoes? 

It’s best to consider your personal style and your overall, day-to-day level of formality with the way you dress. Use our shoe guide above to gauge what classic shoe style seems most fitting.

What is the difference between the Oxford and Derby styles of shoe? 

Although similar, and both dress shoes, Oxford shoes consist of a closed lace system, where the lace flaps sit under the tongue. The slightly less formal option of dress shoes, Derby shoes uses an open lace system where the lace flaps sit on the top of the tongue. 

What is the best way to take care of my classic men’s shoes?

We have an array of shoe care guides and shoe care products available to ensure your shoes stay in tip-top condition. Find the shoe care guide based on your shoe leathers here

What are the most comfortable classic men's shoes?

Finding comfortable dress shoes can be tricky due to the stiffness of the leather to begin with. We always recommend home testing your shoes, keeping in mind they may need a little breaking in time too.