The Ultimate Guide To Men’s Chelsea Boots

While it may have played second fiddle to sneakers for the best part of the 21st century, the instantly recognisable Chelsea boot is still a classic men’s shoe that is long due a renaissance.

From its heyday in the 50s and 60s, the Chelsea boot has gradually taken a back seat to sneakers as the everyday man’s go-to shoe of choice, but when it comes to smart casual dressing you won’t find a more dependable style.

Moreover, many brands have recently taken the Chelsea boot blueprint and run with it, creating chunky contemporary versions that veer into the realm of streetwear.

Whether you’re more of a classic dresser, prefer a rock ’n’ roll edge, or love your fashion labels, the Chelsea boot is a versatile and timeless silhouette you shouldn’t be without. Here’s everything you need to know before adding a pair to your shoe rack.

What to consider when buying Chelsea boots

Shape

A selection of R.M. Williams men's Chelsea boots balanced on rocks

R.M. Williams

The main characteristics that define the Chelsea boot are of course the ankle-height finish, and the fact that the upper is typically made from two pieces of leather with panels of elasticated textile on either side of the ankle. (Although you’ll find some luxury shoe brands producing wholecut boots, i.e. from one piece of leather.)

Otherwise, it’s all about the toe shape. The most traditional designs have a very gradual taper to the toe, which is neither too pointy nor too round. Smarter contemporary styles can sometimes feature a squared-off toe, while casual contemporary styles will often evoke rugged military boots, being much more rounded in the toe. Pointy winkle-pickers should be avoided at all costs, unless you’re attending a fancy dress party as a 70s Miami pimp.

The heels of modern Chelsea boots are in the main pretty low, although the likes of Saint Laurent still offer versions that more closely resemble a classic Cuban heel.

Material

Man wearing brown suede Chelsea boots with grey wool pinstripe trousers

Velasca

Polished box calf leather, soft suede and occasionally vegan leather are the typical Chelsea boot options today. More formal styles tend to come in leather with a beautiful burnished patina, whereas more casual boots will opt for a matte leather finish.

Suede straddles the smart casual divide pretty well and is therefore a very versatile option; black suede being smarter than the popular tan variety.

The soles tend to vary between leather (the smartest) and thin rubber, although chunky versions – whether commando, lugged or Vibram – are a current footwear trend within menswear as a whole.

Style

Man wearing brown leather Chelsea boots with thick lugged sole with mid-wash blue jeans

Velasca

While most Chelsea boots conform to the standard spec – low heel, elasticated panels, leather uppers, rounded toe taper – it’s by no means your only option in 2023. That said, anything that deviates too much from this blueprint is probably not a Chelsea boot (i.e. zip-fastened styles or buckled jodhpur boots).

The classic style can vary in degrees of smartness, with burnished leather options with square toes on the formal side, and rounded-toe suede styles sitting on the casual end of the spectrum.

However, contemporary versions lean much more into a streetwear aesthetic with the addition of chunky soles. The silhouette is probably closer to a military boot than a traditional Chelsea, and is designed to be worn in a more modern context with fashion-forward or designer pieces.

The best men’s Chelsea boot brands

R.M. Williams

As rugged as you would expect from this exemplary Australian bootmaker, R.M. Williams has been selling Chelsea boots since 1932 and has mastered the silhouette, producing over 50 different variations using a couple of unique blocks.

The Craftsman boot is the most popular style and comes in a number of leather and suede upper options, all beautifully handcrafted and built to last.

Shop now: Baltzar

Velasca

Direct-to-consumer brand Velasca works with artisans in Le Marche – the birthplace of shoemaking in Italy – to produce some of the finest Chelsea boots you will find. But not only that, due to a completely integrated supply chain, and by cutting out the middleman, they’re also a fraction of the price of its luxury competitors.

Made entirely in Italy using the finest quality calf leather and suede, Velasca’s Chelsea boots are available in a number of neutral colourways, from formal black to rich tobacco brown. The silhouettes are quite traditional, but there are a number contemporary design touches throughout including chunky lug soles, tartan linings and brogue detailing.

Shop now: Velasca

Cobbler Union

Much like Velasca, Cobbler Union is a brand looking to democratise luxury footwear for us all. The founders cut their teeth at a bespoke shoemaking studio in Barcelona, producing expensive shoes and boots for high net worth individuals, and they have brought this knowledge and expertise to their own direct-to-consumer brand.

As you’d probably expect, the Chelsea boots are faultless. Handmade in Spain using the Goodyear-welt method to ensure longevity and easy resoling, they are sculpted on the brand’s elegant Ritz last, which features a slightly pointed toe.

Available in both suede and leather, our favourite is the Oxblood leather version with its beautifully rich, burnished patina. Ideal for matching with a navy or grey suit.

Shop now: Cobbler Union

Kleman

Founded in 1945, authentic French shoemaker Kleman crafts all its footwear by hand in its factory in La Romagne. Not only that, such is its commitment to being ‘Made in France’, the raw materials used are all locally sourced, too, from European bovine leathers to laces woven 10km from its workshop.

The brand specialises in hardy work shoes and boots, having initially been created for trades that required sturdiness and quality. It must be doing something right, as Kleman has been a supplier for several French public administrations, including the national railway service, Air France, French Customs and even the French Army.

If you’re a fan of workwear or need a casual boot that can stand up to a beating, look no further. The brand’s Chelsea boots feature thick lugged soles, cemented and stitched for durability, and come in a variety of contemporary colourways, including grey, khaki, burgundy and tobacco.

Shop now: Kleman

Dr. Martens

Want more of an edge to your boots? There’s only one option: Dr. Martens. The punk favourite brings the same shit-kicking energy to its Chelseas as it does its iconic 8-eyelet design.

But unlike a moody teenager, Dr. M is not just attitude. The British brand is a legit shoemaker, having been producing its footwear in the UK’s shoemaking capital, Northampton, since 1901.

It may now be owned by private equity group Permira, and the majority of production moved abroad, but the heritage and essence of Docs remains, which gives these Chelsea boots a history and authenticity – as well as an aesthetic – you won’t find anywhere else.

Shop now: Amazon

Clarks

Although better-known for its desert and Wallabee silhouettes, British stalwart Clarks does a fine line in Chelsea boots, too. By far the most affordable option on our list, the modest price points are no indication of quality, with high-quality suede, nubuck and leather uppers (we’re particularly fond of the beeswax version) and cushioned footbeds coming as standard.

If you’re looking for a daily workhorse boot or want to try out the style without spending the earth, you could do a lot worse.

Shop now: Amazon

Saint Laurent

Saint Laurent has always leaned on a rock ’n’ roll aesthetic so it’s no surprise that one of its most iconic shoes is a Chelsea boot. The ‘Wyatt’ is a stunning iteration of the classic, crafted in Italy with a perfectly formed almond toe and available in a number of different hides, from smooth calfskin leather to suede.

The heel verges on Cuban, so if you’re looking for a little extra height, then these might be the luxury step-up you need.

Shop now: MATCHESFASHION

John Lobb

Bespoke shoemaking icon John Lobb’s ready-to-wear collections boast an incredible level of craftsmanship that you’ll find very difficult to surpass.

As far as smart Chelsea boots go, its Kensington model is frankly peerless. A wholecut style built on the brand’s new 0521 last, it’s characterised by its angular and structured toe shape, perfect for combining with a suit.

Shop now: Farfetch

Cheaney

Northamptonshire-based shoemaker Cheaney boasts a fantastic heritage, so you can rest assured that its eclectic range of Chelsea boots are made to exacting standards.

The Godwin model is a traditional shape and perfect for wearing in the city, but we love the brand’s more casual brogue styles, such as the versatile Tamar GV in oiled leather, featuring a chunky sole that can be styled with a modern wardrobe.

Shop now: Cheaney

Edward Green

Edward Green is another Northampton-based company with a long and decorated heritage, having been established in 1890. Since then it has built itself a reputation as one of the finest shoemakers in the world.

Its Chelsea boots are testament to this, available in an array of exquisite hides and lasts. The best among these is the Newmarket in dark oak, handmade using antique calf leather featuring layers of handwork that gives the boot such an inimitable burnished patina.

Shop now: MR PORTER

J.M. Weston

French bootmaker J.M. Weston has rightly earned a stellar reputation for its handmade shoes and boots, which it has been crafting since 1891. All of the exemplary handwork is conducted in a single factory in Limoges, guaranteeing a very high standard of craftsmanship.

Weston’s Chelsea is called the ‘Bottine Cambre’ and references a design from the 70s. Smooth clean lines, vegetable tanned French leather and Goodyear-welted construction all make for a superior boot.

Shop now: MR PORTER

Christian Louboutin

The iconic red soles of Christian Louboutin are very much coveted in the womenswear world, but the iconic shoe designer is less known for his superb men’s collection.

Louboutin’s Chelsea boot range is an expression of the designer’s brilliance, with stunning traditional versions cut from buttery-soft calf leather, contemporary chunky options and some head-turning subversive designs with metal spikes for toe caps.

For a way to spice up black tie attire, the designer’s Roadyrocks patent leather Chelsea comes with a faceted gemstone heel reminiscent of crystal whisky glasses.

Shop now: MATCHESFASHION

Alexander McQueen

Sarah Burton and the design team at Alexander McQueen stole a march on the sneaker world when it first released its chunky lo-fi sneakers, managing to offer a more wearable take on the ‘ugly kicks’ trend.

The brand has retained the theme with its Chelsea boots collection, offering a Hybrid sneaker style that is super versatile, as well as its metal hardware-embellished Stack Chelsea boot and the more minimalist Tread boot.

Each one is imbued with that innate punkiness that McQueen has become so revered for.

Shop now: SSENSE

Crockett & Jones

Another of the fabled Northampton makers, Crockett & Jones has been producing superior Goodyear-welted leather footwear since it opened its doors in 1879. Its craftsmen are some of the best in the business and produce an eclectic collection of Chelsea boots season after season.

As with most heritage makers, Crockett & Jones doesn’t deviate too far from the traditional variations. Expect beautifully burnished calfskin leather designs for the city, as well as more rugged Scotch grain and rough-out suede options for casual-leaning wardrobes.

Shop now: MATCHESFASHION

Santoni

Italian shoemaker Santoni doesn’t do things by halves. Employing over 700 artisans, it is a hive mind of creativity, which is beautifully played out in the most eclectic and imaginative Chelsea boot collection on this list. That’s no small feat, by the way.

From polished brogue designs to sumptuous suede options, Santoni cuts its Chelsea boots differently to most others, with seams that conform to the shape of the foot rather than the traditional method of the leather being joined at the elasticated inserts. The result is undeniably unique and always striking.

Shop now: Farfetch

How to style Chelsea boots

Traditional polished leather Chelsea boots, especially in black or burgundy, are smart enough to wear with tailoring and are a great way to tone down the suit’s formality or just add a little hint of rebelliousness.

For the most part though, the best way to wear Chelsea boots is with a pair of slim-cut tapered jeans, the line of which neatly leads into the sleek dimensions of the boot.

Wider, straight-leg styles tend to jar with the boots’ slim silhouette, and are therefore best avoided. Contemporary versions with chunky, military-esque soles look great with modern techwear and streetwear.

The history of the Chelsea boot

It’s believed that the origins of the Chelsea boot date back nearly two centuries to Queen Victoria’s bootmaker, Mr J Sparkes-Hall, who designed a pair of ankle boots with inserts so that they could be pulled on and off with little effort (although it’s highly unlikely the Queen was putting her shoes on).

Charles Goodyear – the inventor of the Goodyear welt and vulcanised rubber (another term for elastic) – should really take the credit because without him, such an elasticated ankle boot would not have been possible. Back then, they were known as paddock boots and primarily used as a casual shoe for horse riding and general country pursuits. But the look caught on in the early 1900s and became a widely used and popular style right up until World War I.

The ‘Chelsea’ moniker didn’t get applied until the late 50s, when the boot was appropriated by the style makers of Swinging London. The likes of the Beatles (who wore Cuban-heeled versions) and the Rolling Stones repped it for the guys, while female icons such as Jean Shrimpton and Mary Quant made sure the girls got in on the act.

All of a sudden, every hedonist on the Kings Road was rocking a pair, and so they came to be Chelsea boots. They even found their way onto the feet of Stormtroopers in all of the first three Star Wars films.