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

2019-10-24 | Since 8 Month
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.
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.

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...

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.
Would any roundup 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.

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