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10 best men’s winter boots: Chelsea, chukka and hiking styles for the colder months

Seasons are changing and so should your wardrobe – that means investing in solid footwear

Adam Turner
Tuesday 19 November 2019 19:31 GMT
Suede or leather, these boots are guaranteed waterproof
Suede or leather, these boots are guaranteed waterproof

It shouldn’t take a sensational weather story to make you realise things are going to get colder, wetter, and darker from now on – just like every other British winter.

But rather than conform to stereotypes, and complain about the weather to anyone who’ll listen, why not get yourself prepared?

Yes gentlemen, that means spending cash on some decent cold-weather kit. We’re talking heavy duty jackets, thick-knit jumpers, and woolly scarves.

But most important of all, investing in some proper winter boots to keep your feet warm and dry. In our search for the perfect pair, we were looking for durable, watertight shoes with grippy soles.

You can pick up sturdy boots online or from the high street for under £50. Although if you do fancy splashing out (excuse the pun), don’t worry, we’ve picked out some classy, designer options, like a pair of British-made classics favoured by none other than the nation’s favourite secret agent, 007.

You can trust our independent reviews. We may earn commission from some of the retailers, but we never allow this to influence selections, which are formed from real-world testing and expert advice. This revenue helps to fund journalism across The Independent.

Asos design technical hiker boots: £38, Asos

We’re pleased to announce that hiking boots are now in vogue. They’re so on-trend, in fact, that these everyday subtle, black hiker boots by Asos are our top pick. These are lightweight enough to chuck into a rucksack just in case it rains, but sturdy enough to stand up to the elements when it does, and you can’t knock ’em for the price. We particularly like the black-and-white-detailed laces, thick moulded sole, and elasticated, wetsuit-like ankle seals, which do a sterling job at keeping your trotters dry.

Buy now

Sanders & Sanders moss suede hi-top chukka boots: £205, Sanders & Sanders

Steve McQueen may have made hi-top, chukka boots cool, but it was probably Daniel Craig who introduced them to hip millennials. The blue-eyed heartthrob donned a pair of these exact Sanders & Sanders boots in brown, when he played James Bond in Spectre. Money aside, they’d be our number one pick simply because they’re timeless, comfy and effortlessly stylish. We like the autumnal mossy green but they’re available in eight different colours. Consider a half size bigger as they come up a little small and don’t stress about wearing them when it’s raining – it’s quality suede so you’ll be grand throughout the winter.

Buy now

Zara grey split suede leather ankle boots: £69.99, Zara

Everyone from The Beatles to Kanye West has been spotted in Chelsea boots over the years, and once you’ve added a pair to your shoe stand, you’ll understand why. As far as footwear goes, they’re incredibly versatile – try to work from the belief that the pointier the toe, the smarter the occasion. Zara’s round-toe grey suede Chelsea boots, for example, are a solid casual option – perfect for crisper, drier winter days. And the elastic side panels allow you to slip them on and off like a dream. It’s the little things in life...

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Red Wing tan 6in classic moc boots: £269, Schuh

We know the price tag is unnerving, but Red Wing is renowned for making proper hardy footwear for both men and women, so you’ll be able to wear these boots for plenty of winters to come. The Minnesotan company, founded in 1905, began making footwear for industrial workforces and has been knocking out quality leather shoes ever since. Although you’re probably more likely to see a hipster strolling through Shoreditch in a pair than a lumberjack in rural USA these days.

These gorgeous leather moc boots with tidy contrast seams are best worn with a pair of indigo denim jeans or a turned-up pair of light chinos. They’re big fitting so try a size or half-size under, or your heels won’t thank you.

Buy now

Dr Martens vegan 2976 Chelsea boots: from £139, Dr Martens

Would any round-up of the best men’s winter boots be complete without a pair of Dr Martens? Of course not. However, we’ve gone with something slightly less obvious, in the shape of a pair of unisex vegan leather Chelsea boots complete with classic AirWair air-cushioned soles. They look like the real deal, yet no animal products were used in their creation, so you can feel like you’ve done your bit for animal rights. It takes a little while to wear them in, like most docs, but strap up your heels and stick with them. Trust us, this kind of tough love is rewarding.

Buy now

Mango suede desert boots: £89.99, Mango

It’s an icy December night, you’re going to a gig in town and you want to wear a pair of boots that don’t make you look like a naff, undercover policeman. Step forward the trusty desert boot. Desert boots were popularised by British shoe company Clarks in the 1950s, although now everyone – from designer brands to high street retailers – has their own take on this classic boot.

Mango’s offering is your first-class ticket to a nonchalant indie look. These elegant ankle boots are 100 per cent suede and come with a slightly more rounded toe and leather laces, because the devil’s in the detail. Available in sand or chocolate brown and coming in at just under £100, they also prove you don’t have to have Alex Turner’s bank account to pull off rockstar chic.

Buy now

Asos design white leather brogue boots: £55, Asos

Like the look of Dr Martens but not sure about the price? Make these Asos boots your trial run. They’re half the price, have similar punk-ish swagger and come with treads thick enough to skank for hours on end. We’re big fans of the brogue details, high ankle style and handy pull tab – as we know these types of boots can be a nightmare to get off. Use a leather protector to keep that shiny white leather outer looking pristine during winter months, and think twice before dancing through puddles on your way home.

Buy now

Danner bull run 6in: £199, Triads

Before moving his operation to Portland, Charles Danner founded his footwear company back in 1932 because he wanted to make affordable, robust boots for the good people of Chippewa Falls – a then-logging town in Wisconsin. A line on the company’s website reads: “You don’t put on a pair of Danner boots to sit around the house, they’re made for adventure.” We take that to mean stomping around in the rain.

Either way, we’re feeling the spotless details on these black, full-grain leather boots, like the intricate needlework, rounded contrast laces and tiny American flag. They’re not cheap, but you know what they say: buy cheap, buy twice.

Buy now

Asos design Cuban heel western Chelsea boots: £55, Asos

We reckon these neat, black leather western-style men’s Chelsea boots have a Beatlesque quality to them. Maybe it’s just that iconic Cuban heel? Regardless, they’re pretty rock’n’roll – just check out those lightning-shaped elasticated inserts. And don’t let the pointed toe trick you into thinking you can’t wear them with jeans, as they look just as good with a pair of black skinny jeans as they do with a nice suit. They’re a steal at just over £50 – especially as the uppers are made from 100 per cent leather.

Buy now

Grenson Bobby mountain boot: £285, Grenson

Coming in at the higher end of our budget are Grenson’s slick, all-black, military-style men’s leather hiking boots. We’ll make no qualms that they’re pricey, but they’re lovely to look at and can stand up to extreme weather – ideal for this coming winter. What makes us so sure? This British brand produced boots for allied forces during the two world wars, and have over 142 years’ shoemaking experience. Since opening its first Grenson shop in Liverpool Street in 2008, things have gone from strength to strength, with Harrods, Selfridges and Liberty London helping to position the footwear company, not only as a quality, efficient shoe brand but a fashionable one too.

Buy now

The verdict: Men’s winter boots

For boots that’ll keep your feet warm and dry but won’t break the bank, opt for the Asos technical hikers. Have an extra few quid to spend? Treat yourself to Sanders & Sanders’ super-suave, green suede chukka boots.

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