Today, they’re the fashion blogger’s stomper of choice, but Chelsea boots have some right royal history behind them. Harking back to the Victorian era, they 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 it turns out, and added a handy elasticated ankle to the riding boot shape.

Their name unsurprisingly hails from London’s well-heeled Chelsea, where they were the de facto king of footwear during the 1950s and 1960s on King’s Road. It’s no wonder they went mainstream either: they’re one of the most versatile boots for men, the sleek silhouette looking just as good polished to a shine as left gently scuffed for a rock ‘n’ roll patina.

It’s not as simple as just slipping on any old random pair though, oh no. You need to look out for the hallmarks of quality before you reach into your pocket. Dune London’s men’s buyer, Louise Godding, says it’s all in the leather: “The quality of the suede or leather is really key when buying Chelsea boots. 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 heritage menswear item, 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 styling and the boot’s ankle height come into play. “The taller ankle height is very on trend and adds a smarter feel for a sharper look. These look great when worn with slim jeans, a crisp white shirt and a smart wool coat,” Gooding says. Avoid chinos unless you want to look like you’re popping down to the stables.

How to wear men's Chelsea boots

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The Best Brands For Chelsea Boots

Grenson

Grenson has established itself as the go-to for sturdy British-made footwear that champions quality and classic design over trends. True to form, the brand’s Chelsea boots are a masterclass in fuss-free craftsmanship, with each pair taking eight weeks and 200 individual operations to complete.

Buy Now: £245.00

Grenson Jacob Boot

Common Projects

If you thought luxury minimal trainers were where the Common Projects canon ended, let us introduce the label’s equally lust-worthy Chelsea boots, which take that same contemporary stealth wealth design and come stamped with the brand’s signature gold numbering.

Buy Now: £375.00

COMMON PROJECTS Suede Chelsea Boots

Dune

Fans of well-made yet accessibly priced footwear will no doubt be familiar with footwear retailer Dune London, whose frankly dizzying array of Chelsea boot styles means that there’s something here for even the fussiest of men.

Buy Now: £110.00

Dune Natural Sole Leather Chelsea Boot

H&M

High-street stalwart H&M may be best known for its wallet-friendly wares, but now its premium footwear collection provides the perfect happy medium for those looking to go high-end with 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

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. Its range of Chelsea boots leaves no stone unturned, offering a wide range of fresh and familiar takes on this menswear favourite.

Buy Now: £139.00

KURT GEIGER LONDON FREDERICK

ASOS

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

Buy Now: £45.00

ASOS Chelsea Boots In Brown Leather With Black Contrast Sole

Dr. Martens

Dr. Martens can lay claim to making the boot of youth rebellion, but its comprehensive catalogue of styles spans further than that 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: £150.00

DR MARTENS Hardy 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

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 Chelsea boot range expect typically laid-back Aussie design with impeccable performance underfoot.

Buy Now: £460.00

R.M.WILLIAMS Chinchilla Burnished-Leather 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, and not just its famous desert boot.

The brand’s Chelsea boots offer that same solid, no-fuss appeal that your school shoes did all those years ago, but with advanced sole technology that also promises unmatched comfort.

Buy Now: £230.00

Clarks Lorwin Boot

Marks & Spencer

Marks and 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: £360.00

Church's Ravenfield Suede Chelsea Boots

Red Wing

Handmade in the USA, Red Wing’s footwear offering puts good ol’ 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

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: £1,260.00

JOHN LOBB Lawry Water-Resistant Burnished-Leather 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.

Buy Now: £639.00

Saint Laurent Wyatt 30 Boxer Chelsea Boot