Chelsea boots hark back to the Victorian era where they were invented by Queen Victoria’s shoemaker, J. Sparkes-Hall, as an antidote to the lace-up riding boot that was practically impossible to remove by oneself, hence the elasticated ankle piece. Of course, their name was derived from the 1950s and 1960s Chelsea scene, when they were de rigeur on the King’s Road.

They are arguably one of the most versatile footwear silhouettes a man can own, with the boots able to be polished to smartness or left scuffed and dusty for a rock ‘n’ roll patina. Their clean lines, slimline profile and minimal detailing makes them the ideal match for your suits during the working week, yet come the weekend they can be dressed-down with slim black jeans, a simple white tee/shirt and an edgy black biker jacket for an effortlessly cool look that is ideal for a night out.

So, if you want a fail-safe pair of boots ready for autumn, look no further than the ten recommended styles below.

1. Ted Baker Camroon Leather Chelsea Boots

Ted’s Camroon Chelsea boots capture the bohemian vibe of the 1960s perfectly, nodding to the style’s glory days with the incorporation of a paisley print to the blue elasticated side panels.

This fun yet subtle accent is juxtaposed with a gleaming black leather upper and hard wooden sole, adding tone and contrast to this smart, statement design.

Available at ASOS, priced £150.

Ted Baker Camroon Leather Chelsea Boots

2. Dr. Martens Victor Boot

Renowned for its chunky punk-inspired ‘bovver boots’, Dr. Martens has slimmed things down to create this rugged yet refined Chelsea silhouette for the current season.

Lovers of the brand will be pleased to see its signature design features remain intact, including the Goodyear-welted base, air-cushioned sole and, of course, the branded heel loop.

Available at Dr. Martens, priced £115.


3. Cheaney Leather Chelsea Boots

British heritage label Cheaney utilises time-honoured manufacturing processes and the finest materials to produce timeless designs that are built to last a lifetime.

Expect nothing less from these sleek all-black Chelsea boots, which are smart, elegant and able to adapt effortlessly to any occasion.

We’d pair them with a skinny-fit suit for a mod-inspired aesthetic.

Available at Mr Porter, priced £335.


4. Dune Leather Manderin Chelsea Boots

This rich tan leather pair by Dune are sure to get you noticed for all the right reasons.

The worn tan leather gives them a rustic feel, making them the perfect partner to a selvedge jeans and flannel shirt combination, while the round toe and smooth upper will sit just as well with tweed or wool tailoring.

Prepare for these to become your new autumn favourites.

Available at ASOS, priced £99.

Dune Leather Manderin Chelsea Boots

5. Grenson Jacob Chelsea Boot

British label Grenson has been producing premium footwear since the 19th century, so expect nothing less than the very best when you invest in a pair of its shoes.

Case in point, these ‘Jacob’ Chelsea boots are crafted from a beautifully soft tan leather and have been updated with the shoemaker’s trademark punched brogue detailing, Goodyear-welted construction and a traditional leather sole.

Available at END Clothing, priced £205.


6. ASOS Chelsea Boots In Suede

In a departure from standard black and brown iterations, fashion e-tailer ASOS has reimagined the traditional Chelsea boot in a rich navy blue suede.

However, thanks to their muted shade and modern low-cut silhouette, they remain discreet and understated.

Try then with a chambray shirt and dark indigo denim for a head-to-toe tonal look.

Available at ASOS, priced £40.

ASOS Chelsea Boots in Suede

7. Church’s Beijing Chelsea Boot

If slick minimalism is more your style, try this smooth pair by legendary British shoemaker Church’s on for size.

With barely any detailing and a uniform upper and sole, the ‘Beijing’ model brings a touch of understated luxury to the world of Chelsea boots, all while keeping true to the brand’s trademark gentlemanly and refined aesthetic.

Available at Kurt Geiger, priced £310.


8. Zara Leather Chelsea Boots

High street giant Zara brings us a slightly more casual interpretation of the Chelsea boot this season, providing the perfect option for those dress-down days at the office.

Crafted from chocolate brown leather with a somewhat rugged edge, this low-cut pair would make the ideal accompaniment to slim-leg twill chinos and a denim shirt.

Available at Zara, priced £59.99.


9. Russell & Bromley Burlington Chelsea Boot

Like your footwear with a pop of colour? Then look no further than this quirky pair by British label Russell and Bromley.

Seemingly plain on first glance, flashes of bold cobalt blue in the wooden sole add a fun and playful edge to this age-old silhouette, bringing a footwear classic into the modern day.

Available at Russell and Bromley, priced £175.

BURLINGTON Suede Chelsea Boot

10. R.M.Williams Comfort Turnout Suede Chelsea Boots

There’s something slightly Gothic about this all-black pair by Australian outback label R.M. Williams, with the textured suede upper and script branding adding to the mysterious feel.

Handmade on home turf, they’re the perfect accompaniment to rugged outdoors attire and will bring an authentic workerwear edge to any ensemble.

Available at Mr Porter, priced £295.