The Best Men’s Boots for Winter to Add to Your Wardrobe

Tuesday Bote - April 7, 2021

Dressing for cold weather demands that you wrap up well – and you wrap up heavily. In which case, winter clothing tends to involve thicker, sturdier materials that hold up well to snow and ice. Winter footwear, in particular, also needs to be able to keep the wearer from slipping on icy paths or slush-covered sidewalks.

For this reason, winter boots are constructed with thicker and sturdier varieties of leather. The stitching is tighter, more secure, and the soles are heavier, with deeper grooves that allow for stronger traction against slippery surfaces.

But with so many boot brands currently available, how do you choose which one works for you? Likewise, is mere utility reason enough to buy a particular pair of winter boots? Shouldn’t you also consider how well they go with the rest of your winter outfit? 

Well, dear reader, you are in the right place as we give you the lowdown on what you should look out for when it comes to choosing the best winter boots for men.

What Makes a Good Winter Boot for Men?


Before you head out there and choose the best winter boots that work for you, consider the points we’ve presented in our checklist below:

Where will you be wearing your boots?

Most shoemakers or distributors will ask customers if they’re wearing their boots in the city or out in the country. That may not make sense to the potential customer at once, but consider this: the boots you wear to work during an urban winter may not work as well for a winter spent mostly out of doors. Casual winter boots, which are as elegantly cobbled as fine formal footwear, are great if you’re a city slicker. They are sturdy enough to withstand the occasional flurry and have enough traction to keep you from sliding down sidewalks or tripping down frosty steps. Also, you’ll look elegant enough to wear from office to holiday party. 

On the other hand, more ruggedly constructed winter boots have a more weathered, rustic, even sporty look, as these are built to tramp down country roads, explore the forest floor, hike snow-covered peaks, and do rough chores.

How warm do you want your feet to be?

We can sum this up in one word: insulation. Check the product specs as to how well-insulated the boots are, how thick the insulating material used for the boot interiors is, and what sort of insulating material was used. Most reliable brands use synthetic fillers or fleeces like Thinsulate, and many will show how thick the insulation is through what’s called gram rating: the actual weight of the filler is also how much it will keep your feet warm. Lightweight winter boots usually have a rating that spans between 200 to 400 grams; heavy-duty boots can have as high as a 1,200-gram rating, particularly for those used for hunting, fishing, and hiking. Some boots can be adapted to wintry conditions through the insertion of removable felt or fleece insulators.

How high a sole, heel, or top do you need?

Most winter boots can go as high as six or seven inches up a man’s leg, effectively protecting the foot, heel, ankle, and shin against the cold. You could wear shorter-trimmed boots, but you would have to pair these with well-insulated trousers or jumpsuits. 

What’s your personal style?

Are you more of an urban warrior, or are you a true outdoorsman? City slickers would appreciate the elegant, streamlined look of a classic leather boot with the patrician styling of English hunting or jackboots. Those who are into extreme sports will most likely prefer a boot designed much like an athletic shoe: highly insulated synthetic materials, an aerodynamic look, and maximum traction provided by rubber soles grooved with deep cleats.

How much traction do you need?

This seriously depends on how bad winters get where you are. To be extreme about it, you wouldn’t be caught dead (literally or otherwise) in Alaska with leather-soled boots: the grooves in the soles are too shallow to gain traction on heavily snowed-on ground or pavement to be worn safely. In which case, it’s better to err on the side of caution and go for thick, deeply grooved outsoles that will keep you from slipping.

The Best Winter Boots for Men at Your Fingertips

While best known for its increasingly popular line of beautifully crafted leather sneakers, Oliver Cabell continues to prove that it’s anything but a one-trick pony thanks to its growing line of footwear collections for both men and women. Here, you can easily find the best winter boots for men: a hardy yet sophisticated-looking selection that combines the elegance of classic Italian craftsmanship with the strength and durability of a boot that can withstand all but the very worst that winter can throw at it.

The Oliver Cabell men’s boots collection has the following models for your consideration:

  • Mock the Elements | This boot is made with well-polished vegetable-tanned leather from Venice, Italy. It is a study in refined masculinity: a perfect boot for tramping out of doors but sleek and sophisticated enough to wear into the boardroom.
  • Meet Mister Wilson | Oliver Cabell’s Wilson boots are the perfect addition to an urban winter wardrobe. Sporting a design inspired by the classic English hunting boot favored by the – pun intended – well-heeled, these elegant leather boots can easily take you from your commute to work, to power meetings in the boardroom, to the most sophisticated winter galas.
  • Is it SB2 or SB3? | The selections in Oliver Cabell’s SB2 and SB3 series were made for comfort, utility, and rugged good looks. Featuring plush yet durable suede uppers and rippled soles for excellent traction on even the roughest terrain, these boots are as outdoorsy as they get. 

For the Best Winter Boots for Men, Look to Oliver Cabell


Whether you winter in the big city or brave blizzards out in the wilds, the best winter boots for men you can have are the ones from Oliver Cabell.

Made with sustainably-sourced leathers by master craftsmen in ethically-run production facilities, these boots aren’t just made for walking through snowdrifts and slush: they’re made to look good and feel good regardless of the season.


What kind of sole should my boots have to be good enough for winter weather?

Whatever you do, don’t even think of leather soles. They may be good enough for working indoors with polished wood or stone floors, but they won’t stand a chance in either snow or sleet. Worse: you can expect to have a few embarrassing spills as they don’t have any traction. Instead, consider thicker soles made either with natural but weather-tempered rubber or with a sturdy synthetic material like the Vibram Morflex used for the soles of Oliver Cabell’s Mock boots. Consider the outsole’s texture: studded or ridged outsoles will be a much safer bet for wet, slippery, or icy winter terrain. 

I have relatively big feet; does Oliver Cabell have boots in my size?

Oliver Cabell offers boots in the US standard sizes 7, 8, 9, 10, 11, 12, and 13. Note that all boots are made true to size, and you can easily take your normal size. If you want to make sure that the boot fits you well, however, consider the following steps:

  • If you wear a half-size, go up one size if you have a wide foot; or
  • Go down a size if your feet are narrow or of average width.

In any case, the best thing you can do is precisely measure the length and width of your foot, then cross-reference it with the size chart.

How can I maintain my boots? 

Be sure to replace your boot soles before they get too thin for comfort or too smooth for safety. Check with a professional cobbler or shoe repair service to keep soles in check and replace or fix other components such as laces, uppers, and heels. 

Do I need to get a specific boot cleaner for them?

The best winter boots for men demand the best possible care. Especially if you’ve chosen to go with stylish and durable leather boots for the cold season, an Oliver Cabell Leather Kit is an investment you ought to consider. Each kit comes with a stiff-bristled brush, Oliver Cabell’s proprietary Premium Shoe Cleaner, and leather conditioner, which will help keep your boots looking good and in working order for years to come. Note that the shoe cleaner works equally well on conventional glossy leather, suede, and nubuck shoes.