There’s something about leather Chelsea boots that makes it one of the most stylish pieces of menswear. Perhaps its the affiliation with rock and roll culture, perhaps it’s the rebellious relationship it has with the common leather shoe or maybe it’s the lack of laces. Whatever it is, for some reason the common leather Chelsea boot, when worn properly, drips with a sartorial elegance that’s difficult to match.

The leather Chelsea boot is also an extremely versatile boot that has been adopted by a variety of style tribes for a variety of uses. Slim, elegant versions of the boot, closer to its traditional silhouette still persist with tailoring, whilst workwear-inspired chunkier lug sole versions and heftier toe boxes have also morphed from the classic style. Uppers, soles and detailing have all been experimented with to create a myriad of Chelsea boot options to suit different tastes. We’ve pulled together a list of our favourites to provide you with Chelsea boot inspiration no matter the season or occasion. Here’s our pick of the best on the market.

Best leather Chelsea boots for men


The Elfvik leather Chelsea boot from Myrqvist is a beauty. Handcrafted in Portugal from French premium full-grain calf leather with a Goodyear welted construction, the smart boot is finished with a studded rubber sole for longevity, grip and year-round reliability. The premium dark brown calf leather is renowned for its strength and durability whilst a Goodyear construction means renewable soles for a lifetime of wear. A sleek, slender profile and luxurious leather sheen make these boots an elevated smart option for suiting and separates as well as upgrading a pair of jeans.

Oliver Cabell

The Oliver Cabell leather Chelsea boot mixes classic British roots with an Italian-inspired crepe sole for a handsome mix of contemporary European style. Said soles are made from 100% pure virgin Hevea milk, a sustainable tree sap sourced from South America that when processed makes for a robust and comfortable sole. Crafted in Portugal, the classic silhouette boot feature Italian leather uppers sourced from Venice, a vegetable-tanned leather footbed and lining and a hand-stitched lasted sole. A quality take on a classic.


French footwear brand Kleman has experienced a renaissance of late and we think it has something to do with the brand’s ability to apply its own French workwear identity to classic styles. The Tonnant EC Chelsea is a prime example. Available in this dashing shade of cognac and darker, slightly glossy chestnut, the boots feature a heavy cemented lug sole, uppers of suede leather tanned in the brand’s renowned Spanish tannery, and a raw vintage appearance thanks to the use of the leather’s wax treatment. They’re a nice boot to finish off a workwear-inspired fit and a welcome casual Chelsea leather boot option that doesn’t feel overly formal.


For a leather Chelsea boot with a little extra character, consider Velasca’s Lampionèe boot, a luxurious brogue Chelsea in smooth calf leather. A subtle shine and brogue detailing make these Chelsea boots stand out, with a robust rubber sole and heel for comfort and longevity. Smooth, full-grain Italian calfskin leather is used for the boots’ uppers, with the boot itself handcrafted in Montegranaro, in the Marche region of Italy where the country’s traditional shoemaking heritage originates from. They’re an especially formal boot so we’d recommend a well-turned-out cuff trouser or smart pleated chino. An ideal transitional boot for Autumn and Winter.


Aurelien has put its spin on the classic leather Chelsea boot and it’s as Riviera chic as you’d expect it to be. The brand’s City Chelsea boots in brown grain leather have been designed for comfort and versatility, whilst sacrificing nothing on the style front. Handcrafted using supple grain leather, the boots feature handy pull tabs and elasticated sides to allow them to easily slip on and off. An extra padded insole is matched for comfort by the brand’s trademark ivory-coloured rubber outsole, so they’ll comfortably stomp out the miles. Pair with a white chino, linens, or dark denim for a transitional Spring fit.

Common Projects

Minimalist white sneakers but also minimalist leather boots, that’s the Common Projects shtick. The brand’s Chelsea boots channel the same minimalist designs and premium materials, crafted in Italy from smooth leather and set upon a robust, durable rubber lug sole. Sleek uppers but a bit of heft beneath. The subtle gold-stamped numbers are the brand’s calling card, an instantly recognisable mark of quality. A great option for wearing beneath cuffed selvage denim, rock them with a white tee and coach jacket for a minimalist look.


First things first, these Ferragamo leather Chelsea boots are badass. If you’re not into the slimline dainty silhouettes of traditional Chelsea boots, these provide a chunky alternative that still has a smooth calf leather shine. Ideal for balancing wider-fit trousers and capping off monochrome fits but is also a welcome point of difference for finishing a tailored look. Mr Porter describes them as ‘forever boots’ and it’s hard to argue with that sentiment. The smooth leather will soften over time whilst the traditional features of the boot will keep them timeless.

Paul Smith

Last but not least a slim leather Chelsea boot from Paul Smith with the iconic artist's stripes at the top of the elasticated cuff. The brand’s Lansing Chelsea boots have a welcome bit of rock and roll substance to them, with premium leather uppers and soles and a slightly pointier last. Crafted in Portugal, the boots feature elasticated side gores for easy wear and tonal pull tabs to help with getting them on and taking them off. We suggest wearing them with tailoring for a classic look with a twist. Keep that leather nourished and shiny too, they’re a pair for life.

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