Life Skills

Top 5 Men’s Winter Shoe Styles For 2023 (And What To Buy)

  • Dec 1, 2023
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Top 5 Men’s Winter Shoe Styles For 2023 (And What To Buy)

Want to stride through the cold season in style and comfort? Next to securing the perfect big coat, getting your winter footwear game dialled in is priority number one. But don’t assume that means spending the best part of the next six months sewn into a pair of cumbersome leather boots. For those who prefer to keep their ankles free, there are plenty of low-top options available that’ll still keep you warm, dry and looking good.

Winter shoes get less attention than winter boots, but there are plenty of styles around to choose from. These are sneakers and shoes that are either insulated, waterproof, or boast some sort of practical benefit that makes them suited to tackling frosty temperatures and inclement weather. Styles range from sporty to smart, meaning there’s no reason to get cold feet, regardless of where you’re heading. Check out our pick of some of the key variations below.

What Makes A Good Winter Shoe?



Winter shoes don’t have to be waterproof. In fact, some people prefer them not to be, as waterproof often means hot and not particularly breathable. That said, it might be worth thinking about if you live somewhere that’s particularly prone to wet weather.

In order to combat the breathability issues associated with waterproof footwear, the best course is to shop for something with a Gore-Tex liner. This technical fabric has been the gold standard of waterproof tech for decades, allowing water vapour to escape from within, while keeping water droplets from passing through from outside.



If your local winters are notoriously cold, why not consider a winter shoe that provides some level of insulation? This might be something as simple as choosing a sneaker with a bit of padding as opposed to a leather shoe that’s completely unlined, or specifically looking for footwear that has some sort of synthetic or pile insulation built in.



Wet leaves, ice and slippery sidewalks are par for the course during the colder months. Some sole materials are famously poor performers when it comes to these sorts of conditions, with leather, crepe rubber and anything overly flat being some of the main offenders.

To combat this, a good pair of winter shoes should have some sort of grip. This could be provided by a special rubber compound, or even just having pronounced lugs on the sole for increased traction in the wet.



First and foremost, a winter shoe should be capable of standing up to whatever the season throws its way. It should be well built, designed to take some abuse, and made from materials that won’t give up the ghost at the first sign of bad weather.

Forget about things like suede, mesh and canvas. For winter, you want to stick to materials like smooth leather, rubber and tough synthetics.

5 Key Winter Shoe Styles For Men

Commando Sole Derby

The Derby shoe is one of menswear’s all-time greats. It’s a simple design that has been reworked and revisited countless times by countless brands and designers, and it’s as relevant today as it was a century ago. But it does have one downside: it’s not particularly surefooted on slippery ground due to its traditional leather sole.

If you want to continue to enjoy the aesthetic benefits of this classic piece of footwear, one option is to look for one that uses a lugged commando sole in place of a flat leather one. This will improve grip and traction on wet ground, keeping you upright and looking sharp throughout the winter months.

House Shoes

With energy prices through the roof, wrapping up warm at home has never been so important, and a cosy pair of house shoes is a good place to start. These slipper/shoe hybrids range from Birkenstock Bostons to The North Face Tent Mules.

It’s a broad, loosely defined category, but one that became extremely popular during the pandemic. In short, it includes any piece of footwear that’s warm, comfy and designed to be worn around the house, but that has enough of a sole on it to deal with the odd garden-shed mission or quick excursion to grab something you left in the car. Think of them as elevated slippers.

Trail Runners

No one would have predicted it 10 years ago, when everyone was still walking around in Achilles Lows and Stan Smiths, but heavily detailed, teched-out trail-running shoes are now a well-established part of the contemporary menswear landscape.

The shift towards off-road runners was likely a direct result of the trend for bulky, oversized footwear silhouettes that began around 2017. Now it’s impossible to walk through a city centre without spotting at least one pair of Salomons, a sprinkling of Hoka One Ones and maybe the odd La Sportiva if you’re lucky.

Whether you love the look or hate it, there’s no denying that this sort of functional footwear is great for the winter months, boasting excellent grip, comfort and even a Gore-Tex liner here and there.

Rubber Shoes

It’s a bit of a niche category, but there are certain brands making rubber shoes. Think of them like low-top Wellingtons. They’re not exactly versatile from a style standpoint, but there’s no better material when it comes to completely sealing water out.

Even if you’re not wearing them all day, they’re a handy thing to throw on for the commute to work on wet days. And if you buy galoshes, they can actually be worn over your regular shoes to keep them clean and dry in the rain, prolonging their lifespan.

Waterproof Sneakers

There’s no need to stop wearing sneakers when winter arrives, you just need to make sure they’re up to the task. Of all the things to come out of fashion’s recent obsession with functionality and the great outdoors, the abundance of good-looking Gore-Tex products on the market is perhaps the best.

Brands and designers are doing all sorts of weird and wonderful things with this functional performance fabric, including making footwear from it. Check out the likes of Salomon, Arc’teryx, Nike and New Balance for some superb waterproof designs. Converse even makes a Gore-Tex Chuck Taylor now.

Disclaimer: This story is auto-aggregated by a computer program and has not been created or edited by menshealthfits.
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