Few things in the male wardrobe are likely to link reigning monarchs and rockstars. Nonetheless, attracting wearers as diverse as this has been one of the Chelsea boot’s most notable achievements.

Harking back to the 1850s, ankle boots (as they were simply known then) were invented by Queen Victoria’s shoemaker, J. Sparkes-Hall, as an alternative to lace-up riding boots, which were almost impossible to remove unaided. The Victorians were suckers for practicality as well as prudishness so they added a handy elasticated ankle to the riding boot shape.

The name we use today to describe these stylish stompers unsurprisingly hails from London’s well-heeled Chelsea area, where they were the de facto king of footwear during the 1950s and 1960s on King’s Road, be it on the Sloane Rangers that lived there, or the Mod subculture riding through.

It’s little wonder that they went mainstream either, considering they’re one of the most versatile types of shoe a man can own; the sleek silhouette looking just as good polished to a shine as left gently scuffed for a rock ‘n’ roll patina.

Of course, it’s not as simple as just slipping on any old pair, you need to look out for the hallmarks of quality before you reach into your pocket. “The quality of the material is the most important when buying Chelsea boots,” says Dune London men’s shoe buyer, Louise Godding. “Premium, buttery leather will age well and can be polished up easily while adding character to your look.”

When it comes to your suede selection, length matters: in this case, the shorter, the better. “Short-pile suede is a sign of quality and will wear better. Long-pile suede, on the other hand, will get scruffy quickly,” says Godding.

You can learn a lot about the quality of Chelsea boots from the shape of their toes, too. “The curved shape – which is created using heat and pressure on the front of the boot – is key. Any chunky seams or lining creases can rub with wear, so always try them on to check for a smooth finish inside.”

How To Wear Chelsea Boots

As with any menswear item considered a heritage piece, you’ll need to tread carefully when styling to avoid going into turbo toff mode. Gooding’s advice for going more rockstar than rah? “Wear Chelsea boots casually with jeans, a white T-shirt and a ‘thrown-on’ shirt.” Simple.

If you’re looking to sharpen up your act, however, both what you wear and the boot’s ankle height come into play. “A taller ankle height is very on trend and adds a smarter feel for a sharper look,” adds Gooding. “These look great when worn with slim jeans, a crisp Oxford shirt and a smart wool coat.”

As for where you’ll find the best, here are 15 brands delivering on style, substance, and a little more style.

How to wear men's Chelsea boots

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The Best Brands For Chelsea Boots

Grenson

Grenson has established itself as one of the best made in Britain shoe brands, championing quality and classic design over trends. True to form, its Chelsea boots are a masterclass in fuss-free craftsmanship, with each pair taking eight weeks and 200 individual operations to complete.

Buy Now: £240.00

Grenson Declan Boot

Dune

Fans of well-made yet accessibly priced footwear (so that’s everyone, then) will no doubt be familiar with Dune London. The footwear retailer’s frankly dizzying array of Chelsea boot styles — 57 at last count — means that there’s something here for even the fussiest of men.

Buy Now: £75.00

Dune Calzaghe - Tan Desert Chelsea Boot

Common Projects

If you thought minimalist sneakers was where the Common Projects canon ended, let us introduce the New York label’s equally lust-worthy Chelsea boots. Available in both leather and suede, they’re made with the same contemporary stealth wealth design ethos, and come stamped with the brand’s signature gold numbering.

Buy Now: £395.00

COMMON PROJECTS Suede Chelsea Boots

H&M

High street stalwart H&M may be best known for its wallet-friendly wares, but the Swedish firm’s premium line provides the perfect happy medium for those looking to go high-end on their footwear without forking out half a month’s salary. Check out its line of Chelsea boots for swanky stompers at a fraction of the cost that equivalent designer styles would cost you.

Buy Now: £79.99

H&M Suede Chelsea boots

Clarks

If you’re anything like us, your first meeting with Clarks will have been in the run-up to your first year at school. Luckily though, there’s plenty of footwear on offer that’s adult-friendly too. The brand’s Chelseas, like its Chukka boots, deliver the same solid, no-fuss appeal, but with advanced sole technology that also promises unmatched comfort.

Buy Now: £95.00

Clarks Batcombe Top Mens Boot

Kurt Geiger

Kurt Geiger has long been on the front foot when it comes to producing footwear that fuses both classic and contemporary design elements. The retailer’s range of Chelsea boots leaves no stone unturned, offering a broad line-up of fresh and familiar takes on this menswear favourite.

Buy Now: £139.00

KURT GEIGER LONDON FREDERICK

Dr Martens

Ask a Mod, and they’ll tell you that Dr Martens produces the best shoes in the world, but its comprehensive catalogue of rebellious styles spans further than that its iconic 8 eyelet lace-up. The brand’s Chelsea boots take the essence of the original and add some trademark edge to de-gentrify the style.

Buy Now: £135.00

DR MARTENS 2976 SMOOTH CHELSEA BOOTS

Saint Laurent

In the quest for the ultimate designer Chelsea boot, the book well and truly stops with Saint Laurent. The luxury brand has made its name on the back of the Hedi Slimane era rock ‘n’ roll aesthetic, and as such, produces some of the best Chelsea boots on the market. Pair with a leather jacket and an IDGAF attitude.

Buy Now: £639.00

SAINT LAURENT WYATT SUEDE CHELSEA BOOT

ASOS

ASOS is pretty much the Aladdin’s Cave of menswear, so whether you’re feeling skint or flush, adventurous or pared-back, it is sure to have a pair of Chelsea boots that will appeal. It’s practically impossible to leave emptyhanded (or footed).

Buy Now: £35.00

ASOS Chelsea Boots in Brown Leather

R.M. Williams

Australian brand R.M. Williams has a history that stretches back to 1932, so flash-in-the-pan footwear this is not. From its assortment of Chelsea boots, expect typically laid-back Aussie design with impeccable performance underfoot thanks to Goodyear-welted soles.

Buy Now: £350.00

R.M.WILLIAMS Comfort Craftsman Suede Chelsea Boots

Cheaney

Cheaney has long been a key name in the world of English shoemaking, but there’s nothing outdated about its expertly crafted boots, which take that time-tested knowledge and combine it with subtle design tweaks for the perfect fusion of tradition and trend.

Buy Now: £375.00

CHEANEY Godfrey Burnished-Leather Chelsea Boots

Marks & Spencer

Marks & Spencer’s shoes are one its best-kept secrets, punching well above their sub-£100 price point when it comes to quality of materials and craftsmanship. Teaming classic design with surprisingly sturdy construction, the retailer’s Chelsea boots offer the kind of style that never ages.

Buy Now: £79.00

M&S COLLECTION LUXURY Suede Chelsea Boots

Church’s

With a history stretching back well over a century, it’s no exaggeration to say that you’re always in a safe pair of shoes from Church’s. For fans of heritage, craftsmanship and obsessive attention to detail, you’ll struggle to find a finer pair of Chelsea boots.

Buy Now: £390.00

CHURCH'S Houston Leather Chelsea Boots

John Lobb

John Lobb bootmakers can boast of putting footwear on royal feet the world over. If you’re looking for the finest Chelsea boots money can buy, you’d be hard pushed to find a brand with more thumbs ups from the most discerning of men.

Buy Now: £1,325.00

JOHN LOBB Lawry Water-Resistant Burnished-Leather Chelsea Boots

Red Wing

Handmade in the USA, Red Wing’s work boots offering puts good ole American manufacturing front and centre, meaning each pair of Chelsea boots from this stateside shoe supplier have rugged functionality at their core. The fact that they look the part is a welcome bonus.

Buy Now: £269.00

Red Wing 8200 Heritage Chelsea Rancher Boot