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Best Chelsea boots for men 2023: Footwear for smart and casual styling

Stylish, practical and built for all seasons, this is our pick of the best Chelsea boots for men

Few shoes are quite as versatile as the classic Chelsea boot. Made from leather or suede (and occasionally rubber), they’re equally at home completing an outfit whether the dress code is smart or casual. Ideal for city or country, workshops or weekend walks, the elasticated side panels make them much easier to get on and off than a standard boot, as well as super-comfortable.

The first pair of Chelsea boots were apparently designed by Queen Victoria’s bootmaker, way back in 1837. The style was quickly adopted by the equestrian set and was known as the “paddock” boot. It wasn’t until the cool kids and scenesters of that particular neighbourhood of west London got hold of them, in the 1950s and 1960s, that they became known as Chelsea boots. Popularised by the Beatles, Rolling Stones and adopted by the Mods, they’ve remained perennially cool ever since.

Whether you’re looking for some rock star cool, a classic style or something practical for wet weather walking, read on to discover our picks below. First, though, check out our quick guide to buying the best Chelsea boots.

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Best Chelsea boots for men: At a glance

How to choose the best Chelsea boots for you

What is a Chelsea boot?

Chelsea boots are close-fitting ankle boots that  feature stretchy elastic side panels and one, if not two, fabric loops or tabs attached to the rear of the opening that makes it easy for you to pull them on and off. Generally made with a rounded toe and low heel, even the most formal styles are designed for comfort.

What materials are available for Chelsea boots?

Most Chelsea boots are made from either leather or suede. The classic leather finish remains the most popular, since it can be dressed up or worn casually, plus they’re easy to keep clean. Suede offers a more relaxed, comfortable look; but be warned, unless the material comes with a protective coating, they’re a bit of a faff to keep clean in winter.

Alternative materials are available, and our selection includes some made from natural rubber – a superbly practical alternative to the clompy Wellington boot – and vegan leather, which looks and performs almost exactly like the real thing. 

What makes a good Chelsea boot?

If you live in the city, a classic pair of suede or leather Chelsea boots with a rubber sole will offer comfort and practicality for years. Look for waterproof membranes if you want a boot suitable for wet weather, and deep lugs (tread) for extra grip in the mud. Boots made for the workshop or countryside pursuits typically feature thicker leather and more support, but may also take longer to break in.

What about sizing?

Check with the manufacturer about Chelsea boot sizing since some brands recommend taking half a size smaller than usual. This is because the lack of laces means the boot needs to fit snugly. But if in doubt, try before you buy.

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The best Chelsea boots for men you can buy in 2023

1. Blundstone #1308 Rustic Black: Best Chelsea boots overall

Price: £180 | Buy now from Blundstone

Tasmanian brand Blundstone has been making Chelsea boots for more than 150 years, and they remain one of the most popular designs for both urban and country wear. Delivering unisex designs in sizes from UK 3 to 13, they’re tough, weatherproof and comfortable.

We’ve chosen Blundstone’s 1308 design in a gorgeous matte black leather (it’s more grey/green IRL), since these boots feature a classic square toe that appeals to a wider range of people. They also manage to be both smart and casual, depending on your outfit you pair them with. We were seriously impressed by how comfortable they felt, even on first wear – and despite lacking laces, there was plenty of support on offer.  

Well cushioned and with a small heel, the 1308s definitely feel more of a city boot, but the deep lugs on the sole mean they can easily cope with a muddy stomp, as well as being a great go-to pair for pulling on when rushing out of the house.

Key details – Upper: Leather; Sole: TPU rubber

Buy now from Blundstone

2. Ariat Wexford Waterproof: Best Chelsea boots for country pursuits

Price: £180 | Buy now from Ariat

These 100% leather boots are impressively well made and feel like they will last a lifetime. The more you wear them, the better they look, too, with a lovely patina developing on the leather.

The brand, named after a legendary 1970s American racehorse Secretariat, has a long tradition of making premium boots for country pursuits and horse riding. The Wexford boot is probably the least “cowboy” of the collection, although the heel and metal branding does give off a bit of a Western vibe. However, we love the design, and the high-quality leather, with extra comfortable footbed.

Surprisingly, given the heritage of the brand, these boots took no time to break in. If you’ve ever owned a pair of cowboy boots, you’ll appreciate how stiff the leather can be – but thankfully, there are no such issues here.

And it’s the impressive waterproof lining combined with deep rubber tread that makes these robust boots an ideal all-weather option. Mud and puddles stand no chance.  

Key details – Upper: Leather; Sole: TPU rubber

Buy now from Ariat

3. Danner Bull Run Chelsea: Best indestructible Chelsea boots 

Price: £230 | Buy now from Danner

If you’re in the market for a new pair of workwear boots, but want something that’s durable, protective and stylish, then look no further than the American made Bull Run from heritage workwear brand Danner. There are now 14 boots in the range, including Chelsea, moc toe, lace-ups in 6in and 8in, even steel-toe designs – all made from the same, premium full-grain leather.

The leather here is incredibly thick but surprisingly supple, and we love the slip-on practicality of the 6in Chelsea boot design, which is handy if you’re working inside and out of the house or workshop. Obviously, you don’t need to be a carpenter or mechanic to enjoy these boots, but they do look their best worn in, well-oiled and paired with some selvedge jeans. 

The outsole has a generous amount of cushioning for a boot, and despite the lugs not being especially deep, they deliver great non-slip qualities. It also offers protection against electric shocks and the OrthoLite insole is supportive and comfortable, and can be removed when it starts to whiff.

Key details – Upper: Full-grain leather; Sole: Rubber

Buy now from Danner

4. Hush Puppies Shaun Chelsea Boots: Best value Chelsea boots

Price: £70 | Buy now from John Lewis

Whichever finish you choose, whether that’s brown leather, black, brown or sand-coloured suede, you’ll be treated to a stylish city boot that’s impressively made and that offers seriously good value.

Our favourite is the classic sand-coloured suede finish, since it has a relaxed 1960s vibe. Being quite a low boot, it’s also easy to wear with a range of trousers, without ever looking bulky. And for those concerned about whether these will survive the winter, these Hush Puppies have been made using a water-repellent “Worry Free”suede upper that proves surprisingly good at repelling puddles and grime. 

A lightweight design, they feel similar to desert boots on the feet, and there’s a good amount of cushioning from the memory foam insole. Given the low price, these are impressive boots that offer plenty of style for your money.

Key details – Upper: Weather-resistant suede; Sole: Rubber

Buy now from John Lewis

5. Tretorn Terräng Neo Low Winter: Best Chelsea boots for warm, dry feet

Price: £110 | Buy now from Tretorn

Difficult to classify but – once you’ve worn them – hard not to love, this hybrid pair of Chelsea boots are part-wellington boot and part-wetsuit. Okay, so when we say wetsuit, we’re actually referring to the stretchy neoprene lining that offers an incredible amount of warmth, comfort and support. As for being like wellies, these low boots are handmade from FSC-certified sustainable natural rubber and are completely impervious to winter weather.

With two robust tags making them easy to pull on, these could become your favourite winter boots – whether you’re taking the bins out in the rain, gardening, walking the dog or just avoiding wet feet on the commute. A welcome alternative to Wellington boots.

Key details – Upper: FSC Natural Rubber; Sole: Rubber

Buy now from Tretorn

6. Jones Deakin: Best formal Chelsea boots

Price: £110 | Buy now from Jones Bootmaker

Offering a stylish alternative to Oxfords and Brogues in the formal footwear department, this classy pair of boots from Jones is crafted using the highest grade of leather.

They’re smart yet comfortable, with a sheepskin footbed and padded lining making them a joy to wear compared to many stuffy formal shoes. They won’t please the purists – the sole is made from rubber, not leather – but what you lack in traditional craftsmanship you gain in grip.

They deliver a slim silhouette that works well with suit trousers and chinos, and the standard 2cm heel never feels uncomfortable, even if you’re used to trainers. They also offer great value for a proper pair of shoes, and if you’d prefer not to opt for classic polished=black leather, they’re also available in chestnut leather and both brown and tan suede.  

Key details – Upper: Leather; Sole: Rubber

Buy now from Jones Bootmaker

7. Paul Smith Elton: Best Chelsea boots for style

Price: £319 | Buy now from Paul Smith

Available in 100% leather grey suede (shown) or classic polished black (linked), these taller than average Chelsea boots are as stylish as they come. Made in Italy, they have a modern silhouette with an “almond”-shaped toe. And, as we’ve come to expect from Paul Smith, there’s a playfulness to the detailing that comes courtesy of the classic multi-coloured Artist Stripe on the inside section of elasticated fabric.

Unlike more formal Chelsea boots, the soles here are made from hard-wearing but lightweight rubber, and there’s even plenty of foam in the midsole to keep them comfortable all day. But for us, it’s the grown-up but relaxed shape, and pop of colour, that stands these boots out from the rest.

Key details – Upper: Leather; Sole: Rubber

Buy now from Paul Smith

8. Dr Martens 2976 Wintergrip: Best Chelsea boots for rockstar cool

Price: £179 | Buy now from Dr Martens

Initially sold in the 1960s as £2 workwear boots for factory workers, the original Dr Martens were soon adopted by punks. An icon was born, one that remains at the heart of many music and fashion subcultures – even if your dad does still wear them. 

Best known for the classic eight-hole boots, Dr Martens now has a super range of Chelsea boots that, aside from being a whole lot easier to get on and off, blend the original GripWair one-piece moulded soles with long-lasting leather uppers. Choose from various colours, heights and even a bold high-fashion platform style such as the 2976 Quad.

But if you’re looking for a classic punk aesthetic with added practicality, the 2976 is impervious to bad weather and comes with an ingenious insert in the sole that offers significantly more grip than the original design, without ruining the look.

A word of warning to anyone looking to buy their first pair of DMs: the classic leather styles can take a while to break in, so wearing them around the house is advised. But once you have become used to them, you’ll enjoy a hardwearing, long-lasting design that only looks better with age.  

Key details – Upper: Leather; Sole: TPU

Buy now from Dr Martens

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