6 of the Best Winter Boots Brands for Men

by Oliver Stallwood  |  Updated October 14, 2023

Choosing the right winter boots is essential. Far harder wearing than your average sneaker, boots will stay with you in the long run so are better seen as an investment rather than a fashion statement – but shop well and you can have both.

Timberland Euro Hiker (Photo:

Switching from a pair of flip-flops or sneakers to winter footwear can seem like a daunting affair. Boots are often cumbersome and expensive purchases so buying the right pair is essential. But rather than approaching those winter boots as a seasonal, impulse purchase, with an eye to the latest fashion, it makes more sense to buy something that is both functional and timeless – you’re unlikely to wear out a sturdy pair of boots in a few months as you would with sports shoes. With this in mind there are a few companies out there that have not only been reliable partners for feet in cold conditions for many years, they also have a look and feel that won’t go out of fashion any time soon. Here’s five of the best:


When talking about winter boots it’s impossible not to mention Timbs. The brand may have moved more into fashion than outdoors over the years, but staples like the 6-inch Waterproof Boot (which actually comes in nine different colours, not just wheat nubuck) are still the real deal. They take a while to break them in but once you have these boots feel surprisingly comfortable and last so long that you’ll probably forget where you got them in the first place. Alongside this stone cold classic, Timberland has a massive range (with wide options available too) but a special mention should go to the Men’s Euro Hiker Leather Boot. This cult lightweight boot, with a vintage Alpine look pared to a sneaker spec EVA sole, was especially popular in nineties Northern Britain. Get your pair in Medium Brown Full-Grain now. 

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Helly Hansen 

Helly Hansen Men’s Bergheim Hellytech® WATERPROOF Primaloft Insulated Boots (Photo:

Perhaps better know for sailing gear and urban puffer jackets, Norwegian brand Helly Hansen also does a great range of boots perfect for any travelling expedition, whether that’s just an evening of apres ski or a trip to the Arctic. The men’s range of winter boots don’t just look good, they use in-house Helly Hansen tech to create footwear that keeps out the elements at an affordable price. There is also a great range, from rugged cold-weather boots to lighter, waterproof options, such as the Monashee and kelvin, that can be worn on a plane ready to step out the terminal into the elements. 

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Red Wing

Red-Wing Moc 8864 Gore-Tex (Photo:

It’s easy to dismiss Red Wing as a brand best suited to the rugged pursuit of upmarket urban barber shop. However, there is a lot to the brand that has perhaps become forgotten due to its popularity with the more mustachioed members of society. For starters, Red Wing boots are still handmade, and have been for the last 100 years, with an attention to detail that is lost in most brands – even the leather is coloured and finished at the company’s own tannery. Then there is the fact that after a 3D scanned fitting process Red Wing boots go on to mould to the feet, making them more and more comfortable over time. Adding to all this old school construction, Red Wing has also introduced new tech for ultimate winter performance, chucking in waterproof GORE-TEX bootie and fully-waterproof Russet Leather to the 6-inch Classic Moc. 

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Blundstone ‘The Original’ (Photo:

With roots tracing back over 100 years, the Tasmanian boots were mostly seen kicking up dust on worksites or resting on an Outback bar rail. Helped by a boom in travel to Australia in the nineties, Blunnies, as they are affectionately known in the Outback, started appearing on urbanites who wanted something strong enough for rain, mud and snow, but would also go with a pair of expensive jeans. Blundstone did controversially move its manufacturing to Asia from Tasmania just over 15 years ago but has managed to keep the quality control levels high. The Blundstone range can be a bit confusing – The Original Chelsea boot is the one to go for but there are many different variations on the style. We’d just keep it simple in a Stout Brown and let the next ten or twenty years gently weather them into the perfect patina. 

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L.L Bean

LL Bean is probably the most popular brand you may never have heard of. If you think Supreme does a good job of selling out styles, L.L Bean’s Bean Boot can give the NY skate brand a run for its Money Gun. The Freeport, Maine, company famously sells out of its duck boot every autumn – the boot being almost unbeatable at keeping feet bone dry even in deep puddles. It looks a bit gawky but get past the New England amateur logger looks and you have an amazing boot. What’s even more amazing is the price, with the Bean Boots selling for 100 bucks at times. There is an extensive range of other boots, hiking shoes and even a Bean Boots rubber moccasin. A sleeper style for us though is the Storm Chaser 5 – perhaps the best-named pair of waterproof slip-ons on the market.

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Salomon specialises in winter shoes and boots that are both highly functional and good looking. It was no wonder that the sleek Speedcross sneaker made the crossover from trail running to high fashion a couple of years ago, with rugged good looks blending with hard wearing everyday quality. But what makes Salomon, a brand that has been around for more than 70 years, so special is that it stays to its outdoor lifestyle roots, still being run in the shadow of snow capped mountains at its headquarters in Annecy, France. Neither has the company sold out with cheap shoes that flood the high street, or created elitist products with double-take price tags (we’ll allow it the odd Palace collab). Instead the company sticks to proven durability and affordability. The boots err more on the technical side, so you are going to look outdoorsy, but are subdued enough to avoid looking like a trip to the supermarket is an attempt on Everest. Choose something like the Outblast winter boot for a warm, waterproof all encompassing boot with more a comfort-orientated sneaker-style sole for the ultimate do-it-all footwear.

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