With autumn approaching, now is the time to assess your footwear wardrobe and adequately prepare it for the cooler months ahead. Logically, that means boots. Maybe you're a classic Chelsea boot guy through and through, or a desert boot devotee. But before you go reaching for your old faithfuls, may we interest you in another style that's just as deserving of your attention – albeit somewhat underrated? Enter Derby boots.

What are Derby boots?

The boot version of its sibling the Derby shoe, the Derby boot is a rugged and robust footwear staple that's perfect for everyday wear, particularly in chilly weather conditions. With roots in military style, it usually features a sturdy rubber sole and lined leather or suede construction. Like Derby shoes, Derby boots are characterised by an open lacing system (in contrast to the closed lacing style of an Oxford shoe). Laces run all the way from the top of the vamp – the area by the tongue – to the top of the boot, which usually sits a few inches above the ankle.

How to wear Derby boots

When it comes to styling Derby boots, feel free to play around and experiment: just like the Derby shoe, the Derby boot is a multi-functional wardrobe hero that you'll reach for time and again. A fail-safe styling option is to embrace the ruggedness of the boot and team your Derbies with utilitarian-inspired workwear staples. The chunky silhouette will work nicely with a heavyweight worker jacket and cotton twill trousers or raw denim jeans. Otherwise, dress them up with soft tailoring: channel smart-casual style with an unstructured blazer and pleated trousers. For a rugged take on summer style, wear them with belted tailored shorts and a tucked-in tee.

The best Derby boots for men in 2024


French footwear label KLEMAN creates functional worker shoes that marry timeless style with uncompromising durability. Its OLAN OLOW boots are designed in collaboration with OLOW, a French eco-clothing brand. Ethically manufactured from carefully selected European leathers, they're mounted on KLEMAN's EDITO grip sole, known for its anti-slip and anti-abrasion properties. Sustainable and stylish, what's not to love?

Myrqvist Tjärnö Dark Brown Calf Boots

These sturdy men's Derby boots from Swedish footwear label Myrqvist are all-weather wonders, made with a 360° storm welt for water protection, and a double studded rubber sole for extra traction and support. The construction uses full grain calf leather from the renowned French tannery Du Puy, so you know they're built to last. Team them with selvedge denim jeans and a corduroy overshirt for a rugged workwear-inspired look.

Velasca Pacciasass Boots

Made in the Italian shoemaking district of Montegranaro, these Derby boots from Velasca epitomise the traditional values of Italian craftsmanship. Suede calfskin forms the upper while the naturally flexible sole is made from Para rubber, which comes from smoked lattice plants of Brazil. With an emphasis on quality of materials over extraneous aesthetic details, these boots – like all Velasca designs – are timeless in style, underpinned by a refined Italian elegance.

Cheaney Pennine II C Veldtschoen Derby Boot

Cheaney's Veldtschoen Derby boot will have you looking the part, whether you're walking through muddy country fields or commuting across the city. Hand finished in burgundy grain leather and set on a Goodyear welted Veldtschoen Commando rubber sole, these tough boots are made to stand the test of time. Style them with double-denim for an effortless America-tinged look.

Grenson Augustus Boot

British footwear label Grenson has been making some of the country's best-loved boots for over a century, so it's safe to say they know their stuff. To see what all the fuss is about, give the Augustus boot a go. This chunky style is made from a fine-grained Colarado calf leather and features all-round leather storm welts and a lightweight rubber sole. The ultimate winter boot doesn't exi––

For more timeless boot styles, check out our round-up of the best suede boots for men.