Ride On: The Best Chelsea Boot Brands For Men

For an item of dress to be both rock ‘n’ roll and routinely worn by Australian farmers may seem paradoxical, but it’s something the Chelsea boot has been managing for generations. These elasticated leathery workhorses are as versatile as they are visually appealing – something that has earned them a well-deserved spot in the footwear hall of fame.

An ally to tailoring and a fail-safe accompaniment to your weekend wardrobe, the Chelsea boot is a genuine all-rounder and a must-have in every stylish gent’s arsenal. Here, we explore everything from its rich heritage to where to purchase the perfect pair.

What Are Chelsea Boots?

Myrqvist

 

You may already be well versed on the intricacies of different boot styles, but assuming you’re not, allow us to fill you in: a Chelsea boot is, on a fundamental level, any ankle-high leather boot with elasticated panels at either side to aid putting it on and taking it off.

The style was first created by Queen Victoria’s shoemaker, J Sparks-Hall, who claimed that “She (Queen Victoria) walks in them daily and thus gives the strongest proof of the value she attaches to the invention”. It soon became popular for horse riding and walking, and robust versions featuring thick rubber soles and even steel toe caps started to make their way into workwear.

Fast forward to the 1950s and 1960s and the boots became highly fashionable on the back of the Swinging London scene. It’s thought that their association with the city, and in particular the King’s Road in Chelsea and Fulham, is how they got their name.

How To Style Chelsea Boots

Aside from their stripped-back, stylish looks, the greatest thing about Chelsea boots is their versatility. This is footwear a man can wear at work, play and everywhere else in between.

Office

It doesn’t matter whether your work dress code requires you to don a suit or simply a T-shirt and jeans, a pair of Chelsea boots will add a touch of flair. For corporate offices, opt for a sleek leather pair and match the colour to your suit (a navy suit with brown Chelsea boots and a grey suit with black Chelsea boots, for example).

It’s also important to make sure your trousers break in the right place. The hem should sit just above the ankle without revealing the top of the boot. For a more relaxed business casual look, try teaming brown suede Chelseas with black denim and a flannel shirt.

Party

Whether it’s a cocktail party, wedding or a big date, this elegant footwear option will see you right. For an outfit that works for all the aforementioned occasions and more, try an eye-catching suit or contrasting trouser and blazer separates with a tonal roll neck and leather Chelsea boots.

Casual

The Chelsea boot is a casual shoe first and foremost, making it a great choice for everyday wear. A reliable companion to everything from selvedge jeans to chinos, it can easily be dressed up or down based on the day’s activities.

For a foolproof look that requires almost no thought, pair dark wash jeans with a classic white T-shirt and suede jacket or overshirt. If you’re looking for something smarter, try cotton twill khakis with an Oxford button-down and lightweight sweater, finished with a blazer or leather motorcycle jacket.

The Best Brands For Chelsea Boots

You know what they are and you’re equipped with the knowledge you need in order to style them. Now allow us to walk you through the best brands for Chelsea boots and why they’re worth giving your money to.

Velasca

Key Style: Magut

If you’re looking for an Italian-made Chelsea Boot with added sprezzatura look no further than the artisanal-minded Velasca. Made from full-grain, smooth calfskin leather with a sturdy and durable vibram rubber soul, the brand’s Magut boot offers an extremely durable yet elegant option for a solid winter Chelsea option.

Buy now at Velasca

Oliver Cabell

Key Style: Chelsea boot

After making its name creating luxe, minimalist sneakers without the usual brand mark-ups, Oliver Cabell moved into more formal footwear styles, and brought the same transparent pricing with it.

The brand’s Chelsea boots take the classic silhouette and craft it with high-quality Italian leathers. Like all the best Chelsea boots, theirs are sleek and sophisticated but have an everyday, highly wearable quality to them.

Buy now at Oliver Cabell

Myrqvist

Key Style: Granhult

Goodyear-welted construction is difficult to come by without a heavy price tag attached. That’s not the case at Stockholm-based Myrqvist. The brand’s Chelsea boots are handcrafted in Portugal and there’s a choice of styles, with some designs coming made from a single piece of leather, while others are winter-ready with a commando sole.

Buy now at Myrqvist

Kleman

Key Style: Tonnant

French brand Klemen brings something rougher and tougher to the Chelsea boot market. Its chunky designs, often sat on a commando sole, sometimes remind us of a work boot. Not all of them, though. Others have dramatically shaped collars and come in faux snakeskin burgundy leather.

In other words, if you’re looking for a Chelsea boot that breaks the mould, this is a fine place to start.

Buy now at Klemen

Common Projects

Key Style: Suede Chelsea

Italian-American luxury footwear label Common Projects may be the last word in premium sneakers, but that’s by no means where the brand’s talents end. Aside from its now-iconic Achilles Low shoe the silhouette for which CP is best known is probably its Chelsea boot.

Expect the finest materials, Italian craftsmanship and trademark gold numbering to the heel. Buy it in suede for an easy-to-wear, everyday option.

Buy now at MR PORTER

Amberjack

Key Style: The Chelsea

Designed in Brooklyn, NY and produced in one of Portugal’s top factories, The Chelsea by American footwear brand Amberjack is arguably the most advanced boot on this list. Crafted using the highest quality leather, sourced from some of the best tanneries in the world (which Amberjack are also partners with), it features heat-activated arch support and laser perforated uppers for all-day comfort, along with a mechanical designed, proprietary outsole that provides support where you need it while guaranteeing longevity.

Available in a selection of versatile colourways, they’ll combine effortlessly with everything in your wardrobe and quickly becoming your go-to shoe.

Buy now at Amberjack

Saint Laurent

Key Style: Wyatt

You can’t have Saint Laurent without boots, and you can’t have boots without Saint Laurent. The French fashion house’s Wyatt silhouette has long been a staple in its collections – sleek, simple and oozing Parisian cool. Best worn with slim black denim and a black leather jacket. Bonus points if they’re all Saint Laurent too.

Buy now at END.

Tricker’s

Key Style: Henry Brogue

Northamptonshire-based shoemaker Tricker’s is a company with serious pedigree. Since 1829, the brand has been the manufacturer of choice for heavy-duty country footwear for England’s estate owners and landed gentry. These aren’t your typical low-profile, slim-fitting Chelsea boots, though. Instead, expect commando soles, brogue detailing and premium touches like Goodyear-welted soles and hand-stitched uppers.

Buy now at Tricker’s

Grenson

Key Style: Declan

Speaking of Goodyear welting, historic British shoemaker Grenson was the first brand to utilise the process. The label, which also hails from Northamptonshire, has since developed a reputation as one of the finest purveyors of footwear. Not just in Britain, either, but the whole world. If you want a pair of Chelsea boots built to stand the test of time, Grenson should be at the very top of your list.

Buy now at Grenson

Clarks Originals

Key Style: Clarkdale Gobi

Clarks Originals is best known for its casual, laid-back silhouettes like the desert boot and the Wallabee. However, its Chelsea boots shouldn’t be sniffed at. With Clarks, you can always rest assured you’re getting the best possible bang for your hard-earned buck. We’re talking unrivalled durability, quality construction and superb, timeless looks. And all for under £100? We challenge you to find a better deal than that.

Buy now at Amazon

R.M. Williams

Key Style: Gardener Whole-Cut

Borrowing its name from its founder, a travelling labourer and bushman who became a millionaire thanks to his leatherwork, Australia’s R.M.Williams is known the world over for producing some of the finest boots money can buy. Its Chelsea boots are no exception, featuring smooth, soft leather upper, sturdy soles and the sort of versatile styling that could take their wearer directly from bush to boardroom.

Buy now at MR PORTER

Dr Martens

Key Style: 2976

Chelsea boots can be stompers too. Just ask the good folk at Dr Martens, who bring the brand’s distinctive DGAF stylings to the traditionally sleeker design. There are a few dozen designs to explore from the classic yellow-stitch style to patterned or even quilted Chelsea boots. To be honest, they’re all great, the chunky dimensions subverting the usually slimmer silhouette. Your black jeans deserve a pair.

Buy now at Farfetch

Crockett & Jones

Key Style: Chelsea VIII

It’s difficult to look past Crockett & Jones in any footwear circle, and its Bonnie boot doesn’t disappoint. A classic silhouette with traditional ‘V’-shaped side elastics, it is made from the finest calf leather or suede and comes complete with City rubber soles for added traction.

Buy now at Pockets

Loake

Key Style: Emsworth

With nearly 150 years of heritage behind it, Loake does contemporary takes on classic footwear. The Chelsea boots are just lovely. Elegant profiles and sublime leathers sit on Goodyear-welted sole units and there are a number of lasts to choose from to make sure you get the perfect fit. Its chestnut-coloured leathers are particularly beautiful.

Buy now at Loake

Celine

Key Style: Hector

What’s a luxury rock n roll brand without an excellent line-up of ankle-high boots? Celine Homme, under the creative direction of Hedi Slimane, brings a mix of punk and glamour to the Chelsea boot. Think pointy toes, Cuban heels, biker embellishments and shiny calfskin leather. All of which look sublime with a pair of skinny black trousers.

Buy now at Celine

Blundstone

Key Style: #500

If you want a rugged Chelsea boot, look no further than Blundstone, an Australian brand that’s been making hard-wearing boots since the 1800s. Its Chelsea styles span the whole spectrum from safety boots to dress boots, but it’s the designs that sit somewhere in the middle that we like the best. Built on strong sole units with shock absorption for extra comfort, the solid design looks great with denim and workwear.

Buy now at Amazon

Paddy Maddison

Paddy Maddison is Ape's Style Editor. His work has been published in Esquire, Men’s Health, ShortList, The Independent and more. An outerwear and sneaker fanatic, his finger is firmly on the pulse for the latest trends, while always maintaining an interest in classic style.