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The instantly recognisable Chelsea boot is a classic men’s shoe that is long due a renaissance and we think we’ve selected the best men’s Chelsea boots on the market today.
From its heyday in the 50s and 60s, men’s Chelsea boots have 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, men’s Chelsea boots are a versatile and timeless silhouette you shouldn’t be without.
In this guide we’ll show you:
- What to consider when buying Chelsea boots (buying tips)
- 16 of the best Chelsea boots for men (best brands)
- How to style Chelsea boots (outfit inspiration)
What to consider when buying Chelsea boots
R.M. Williams
Shape
The main characteristics that define Chelsea boots 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.
The most traditional Chelsea boot designs also 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.
The heels of the best men’s 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
Polished box calf leather, soft suede and occasionally vegan leather are the typical Chelsea boot material options today. More formal styles tend to come in leather with a beautiful burnished patina, whereas more casual Chelsea 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
The best Chelsea boots usually conform to the standard spec – low heel, elasticated panels, leather uppers and rounded toe taper. Anything that deviates too much from this blueprint is probably not a Chelsea boot (i.e. zip-fastened styles or buckled jodhpur boots).
This classic Chelsea boot 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.
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.
16 of the best Chelsea boots for men
Tom Ford
Tom Ford Hainaut Burnished-Leather Chelsea Boots
Tom Ford Suede Boots
Founded in 2005, the luxury American fashion house Tom Ford is known for its refined, contemporary menswear and accessories. Each piece from the brand is meticulously crafted with an emphasis on elegance and detail, and its Chelsea boots are no exception. Tom Ford’s commitment to quality means its footwear is made with premium Italian leathers and assembled by skilled artisans, combining modern design with old-world craftsmanship.
Renowned for sleek silhouettes and subtle sophistication, Tom Ford’s Chelsea boots are designed for the discerning dresser who appreciates a blend of luxury and functionality. These boots feature sleek almond toes, elasticated side panels, and an impeccable finish that speaks to the brand’s high standards. The outsoles are crafted for comfort and durability, ensuring they hold up for any occasion—from polished formalwear to elevated casual looks. Available in a range of timeless hues like black, deep brown, and charcoal, with occasional seasonal colors, Tom Ford’s Chelsea boots are an investment in both style and substance.
Kleman
Kleman Escadron Chunky sole Chelsea boots
Kleman Tonnant EC Chelsea boot
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 men’s Chelsea boots feature thick lugged soles, cemented and stitched for durability, and come in a variety of contemporary colourways. As well as the black and brown classic colours you can also get these men’s Chelsea boots in grey, khaki, burgundy or tobacco.
R.M. Williams
Black Yearling Leather Wentworth G Boots
Greasy Kip Brown Leather Gardener G Boots
As rugged as you would expect from this exemplary Australian bootmaker, R.M. Williams has been creating men’s 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. Whether you’re looking for black Chelsea boots or brown, you won’t go far wrong with R.M.
John Lobb
Kensington
Lawry Suede Chelsea Boots
Bespoke shoemaking icon John Lobb’s ready-to-wear Chelsea boot 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.
Dr. Martens
Dr. Martens Fellside Sd St Chelsea Boot
Dr. Martens Heeled Chelsea Boot
Want more of an edge to your boots? There’s only one option: The men’s Dr. Martens Chelsea boots.
This punk favourite brand brings the same sh*t-kicking energy to its men’s Chelseas boots as it does its iconic 8-eyelet design.
But unlike a moody teenager, Dr. Martens 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 and is world renowned for producing some of the best Chelsea boots for men.
Whilst it may now be owned by private equity group Permira, and the majority of production moved abroad, but the heritage and essence of Dr Martens remains, which gives these Chelsea boots a history and authenticity – as well as an aesthetic – you won’t find anywhere else.
Saint Laurent
Wyatt Suede Chelsea Boots
Wyatt 40mm Suede Chelsea Boots
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.
Cheaney
Tamar GV Chelsea Boot in Husk Eco Oiled Leather
Godwin Chelsea Boot in Black Calf Leather
Northamptonshire-based shoemaker Cheaney boasts a fantastic heritage, so you can rest assured that its eclectic range of Chelsea boots for men 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.
Edward Green
Newmarket Leather Chelsea Boots
Camden Suede Chelsea Boots
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 Chelsea boots in dark oak, handmade using antique calf leather featuring layers of handwork that gives the boot such an inimitable burnished patina.
J.M. Weston
Leather Chelsea Boots
Rubber Sole Chelsea Boot
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.
Christian Louboutin
Motok Leather Chelsea Boots
Black Samson Chelsea Boots
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 Chelsea boot collection too.
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.
Velasca
Magut Dark Brown Suede Calf Leather
Bagaj
Direct-to-consumer brand Velasca works with artisans in Le Marche – the birthplace of shoemaking in Italy – to produce some of the best 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.
Alexander McQueen
Exaggerated-Sole Leather Chelsea Boots
Black Hybrid Chelsea Boots
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.
Cobbler Union
Benjamin – Museum Oxblood – Ritz
Benjamin – Museum Cognac – Ritz
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.
Looking for men’s suede Chelsea boots or perhaps in leather, Cobbler Union have you covered. Our favourite are the Oxblood leather Chelsea boots with a beautifully rich, burnished patina. Ideal for matching with a navy or grey suit.
Crockett & Jones
Leather Chelsea Boots
Leather Chelsea Boots
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.
Clarks
Clarks Clarkdale Gobi Chelsea Boot
Clarks Jaxen Chelsea Boot
Although considered a brand that might make some of the best men’s Chelsea boots, British stalwart Clarks does a fine line of everyday wear boots.
Clarks men’s Chelsea boots are by far the most affordable option on our list. The modest price points are no indication of quality either 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 men’s Chelsea work boots or want to try out a style without breaking the bank, you won’t go far wrong with Clarks.
Santoni
Perforated Leather Ankle Boots
Leather Ankle Boots
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.
How to style Chelsea boots
Hackett
Tiger of Sweden
Bonobos
AllSaints
Traditional polished men’s 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.
If you need some more inspiration on what to wear with Chelsea boots, we recommend you check out this article – 19 Modern Chelsea Boot Outfits For Men