There’s a leather boot out there for every man’s wardrobe. It could be a polished Chelsea bridging the gap between smart and casual or it could be a trustworthy day to day ankle boot. A beloved ankle boot worn so much that resoling can almost be planned annually on the calendar. A great leather boot is a work of art. Hand-crafted from carefully considered materials, hundreds of production steps and welted sole that means it can be resoled for eternity. 

Leather boots are a lifetime investment and a must have. Whether you’re considering something with a commando sole for longevity or a more refined option for special occasions, there’s something, whether it be a black boot or winter boot, out there to suit every man. Here’s a carefully curated pick of our favourites.

Best leather boots for men in 2024

Kleman Combat MD

Like many of the best clothes out there, the commando boot has origins in the military. The original rubber commando sole was pioneered by British company Itshide in the 1930s, changing its output from toys and brushes to tank tracks and torpedoes during the war. The commando sole was another part of its military effort output and the functional nature of the boot stuck. Kleman’s Combat MD is a polished take on the pragmatic leather boot, available in burgundy or cognac Italian leather depending on your tipple. Up top there’s a polished formality, whilst those all important chunky logs on the bottom will ensure faultless grip.

Velasca Magut

The Magut leather boot from Velasca is a classic Chelsea made from smooth calf leather, with  a calf leather lining and a vibram rubber sole and heel. A sturdy, leather boot option for city getup, notice the slightly wider last shape at the front, a welcome detail for those who are in the market for a Chelsea but don’t get on with narrower shaped boots. It’s this slightly more substantial silhouette that makes the boot a versatile option for dressing up with business attire or down with a chino trouser.

Oliver Cabell SB 1

Sometimes you just need a well-built, minimal detail leather boot. It’s no surprise to see minimalist sneaker champions Oliver Cabell making them. The world needs well-built minimalist footwear and OC are here to deliver. The SB1 leather ankle boot in black is a classic lace-up service boot, made from water-resistant full-grain vegetable tanned leather (sourced from a small tannery in Albacete, Spain), with a custom anti-slip rubber outsole from England. The boots are hand-stitched and lasted in Albacete, Spain and they’re a versatile option for everyday wear.

Myrqvist Funäs

The Funäs boot from Myrqvist is a fashion-forward leather boot style, with a nod to function and bootmaking craftsmanship. Made from black country calf leather, the wholecut boot features a sleek central zipper for a truly modern look as well as practical wear. Handcrafted in Portugal, the boots feature a robust hiking sole, a faux shearling lining and leather zipper tab. The fashion-forward shape and traditional materials means they’ll suit larger silhouetted trousers and sleek monochrome looks. Nice to see something different, a big tick in the very cool box.

R.M. Williams Craftsman Chelsea Boots

R.M.Williams is a serious heritage bootmaker and impeccable craftsmanship goes into each boot they produce, whether that be a practical outback style or something a little sleeker like this for formal wear. All of the brand’s leather boots are handmade at their Adelaide factory to this day. The craftsman leather Chelsea boot, a Mr Porter exclusive, is based on a traditional outback riding boot designed in 1932, and comes in a polished cognac leather. First and foremost a formal boot, with its sharp pointed toe, pair it with tailored separates or a smart trouser.

Mr P. Jacques

These Mr P Jacques full-grain leather brogue boots offer a rugged outdoor style option whilst celebrating materials and craftsmanship, hence the brand’s craftsmanship code status. Crafted from buttery soft full grain-leather and built upon Vibram rubber Eton eco lite soles, these lace-up leather boots carry a stylish heft and the broguing detail certainly sets them apart. Wear them beneath your best selvedge denim, chunky knits and a trench or peacoat.

Yuketen Vettore

Well well, what do we have here? A padded ankle boot reminiscent of a hiker but also with a sleek leather attitude? Very cool indeed. Yuketen prides itself on its meticulous quality and the skill and passion of the dedicated hands that craft each leather boot. All of the components that go into each boot from the Italian-made Cortina lug soles to the handsewn beeswax-coated thread are meticulously considered. The Vettore leather boot is one such aesthetic masterpiece, with the craftsmanship and materials to back it up.

Red Wing Blacksmith

You can’t talk leather boots and not include Red Wing. Sorry, don’t blame us, that’s just how it is. Them’s the rules. The heritage US bootmaker isn’t just about those six inch moc toes. There’s other strings to the bootmaking bow. More than 230 steps go into the making of these Blacksmith leather boots (also available in brown), from selecting premium grade leathers to hand-stitching the welt and sole. The 'Briar Oil Slick' leather is hard-wearing and water-resistant and the Vibram mini-lug soles are Goodwear welted for longevity and resoling potential. Rock them with jeans and a premium white tee for that all-American look.

For more like this, check out the best men's Chelsea boots in 2024.