6 Types Of Boots Every Man Should Own For Winter 2023

Is your current winter footwear giving you cold feet? Finding the right boots to help you stride through the cold weather in style can be a challenge. As shoppers, we’re often forced to choose between something that’s warm, waterproof and practical, and something that looks good. As a result, sacrificing style for comfort when the temperature drops is all too common. But it needn’t be.

There are a number of boot options with a foot in both camps. They’re hard-wearing, winter-ready and great looking too. The secret is knowing what styles to search for and where to buy them. And that’s where we come in.

We’ve spent years scouring the web and the real world for the perfect winter boots, and we’ve picked up some great options along the way. We also know what the key ingredients are that make a great piece of cold-weather footwear, so we’ve used that knowledge to compile a handy buying guide to help you in your quest.

Whether you’re looking for a timeless leather boot you can repair, resole and rely on for years to come, or something sporty and modern that won’t give up the ghost when the weather turns sour, you’ll find something that fits the bill below.

What Makes A Good Winter Boot?

Durability

Durability is what boots are all about. If it’s not built like a tank then you might as well be wearing a pair of sneakers. A tough-as-nails exterior and high-quality build is the first thing you should look for when buying a pair of winter boots. That way you won’t find yourself shopping for another pair this time next year.

Grippy Tread

The ground can get super slippy when the weather is wet and cold, so it’s a good idea to get something that’s designed to keep you upright when it does. A nice lugged tread will help to grip on ice-rink pavements, bite into mud and slop, and ultimately help you to preserve your dignity when walking around town on winter days.

Waterproof

Winter boots don’t have to be fully waterproof, but if you live somewhere seriously wet then it might be something worth considering. The trade off is that your boots will be less breathable, which can be wet and uncomfortable in its own right.

Water-Resistant Materials

A better idea is to only choose materials that offer some level of water resistance and aren’t prone to spoiling in the wet. That means a big no to suede and a resounding yes to thick, oily leather.

Warm

It’s also possible to get boots that are insulated in some way. This is a good option for those who experience severe cold in their local area.

Some boots, like Sorel’s iconic Caribou winter boot, use a faux sheepskin lining to trap heat, while others use synthetic insulation like Primaloft to keep the cold at bay.

Key Winter Boot Styles

Duck Boots

These rubber-trimmed stompers are perhaps the ultimate winter boots. They’re designed specifically to tackle snow, rain and cold, and are supremely warm and waterproof. They can be tricky to style, but there are some good-looking options out there, and there’s really no better option if what you want is complete weather protection.

As mentioned above, Sorel is a key brand in this category, and has been making rubberised snow boots for a very long time. For a more fashion-forward take, check out Sperry or Diemme.

Beefed-Up Derby Boots

The Derby boot is a timeless classic that can be worn with anything from casual clothes to tailoring. It’s a must in every man’s wardrobe, and if you buy one with a beefed-up sole unit, there’s no reason this style can’t carry you through the winter months and beyond.

What you need is a thick, ‘commando’ tread. It’s a heavy, lugged sole that grips well and offers steady footing in the wet weather. Alternatives that look – and perform – just as good include ‘Vibram’ and ‘Para’ soles.

Brands that define this sector usually have a workwear edge, so think the likes of Tricker’s, Wolverine, Red Wing, Kleman et al.

Work Boots

Rough, tough, heavyweight, lugged and ready for action, traditional work boots are built to take a battering, whether it’s in the workshop or out in the woods. Their tough-as-nails construction and grippy treaded soles make them perfect for navigating the winter months, and with the occasional resole and repair, the right pair could last you ten or even twenty years. What’s more, they go great with casual clothing – winter wear in particular – and will [aor perfectly with things like flannels, overshirts, jeans and parkas.

There are a number of great brands that specialise in this type of footwear. Perhaps the best known is heritage American label Red Wing, whose rugged leather boots have been keeping the USA’s blue-collar workers shod for well over a century. Check out Danner, Timberland and Thorogood too.

Waterproof Sneaker Boots

Sneakers are far from the most practical footwear when the weather takes a turn for the worst, but with a Gore-Tex liner here and an extended cuff there, some brands have managed to make them seasonally appropriate. These are athletic shoes masquerading as boots. They boast all the comfort and sporty looks of their low-top counterparts but with the increased grip, support and weather protection of those loftier alternatives.

Several of Nike’s classic styles have had the sneakerboot treatment over the years. Our personal favourite was the mid-top Air Max 95 that launched a few years back, but there’s also a duckboot version of the Air Force 1 that’s still available to buy today.

Adidas Terrex is another name worth looking out for. The adventure-sports arm of the German sports giant makes some excellent hiker-cum-sneaker type footwear, such as the Freehiker GTX, which combines comfort, style and technical materials seamlessly.

Chunky Chelseas

Thanks to the single-piece uppers and laceless design, Chelsea boots are excellent in inclement weather. Even better if they’re mounted atop a big, bulky commando sole to grip the ground when it gets wet and slippery.

For premium traditional options, take a look at what the likes of R.M. Williams and Blundstone are doing. Or for something a bit more modern and quirky, we’d suggest brands like Diemme, Velasca and Myrqvist. Dr. Martens makes some excellent options too.

Traditional Hikers

Classic leather hiking boots might have been replaced by lightweight, high-performance, synthetic versions these days, but they still look great and provide excellent protection against the elements during the winter months. They go nicely with workwear pieces like selvedge denim, flannels and chore jackets, and if you buy right they’ll last you for many years to come.

Our favourite brand when it comes to traditional hiking boots is Danner. This historic American brand has been making incredible boots for the best part of a century and has created a number of icons in the process. The Mountain Light is perhaps the most recognisable model and has even been worn by James Bond himself.

Contemporary Hikers

Since outdoorsy stuff became cool, several brands have started making fashion-forward hiking boots using technical materials and modern silhouettes. They’re not as straightforward to style as classic hiking boots, but if you’re looking for a winter footwear option with character, this could be a good option for you.

Check out brands like Roa, Diemme, Hoka One One and Moncler.

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