The Best Winter Boots For Men 2021 - Fashion Daily Tips

The Best Winter Boots For Men 2021

Cold feet are a fact of winter, as reliable as dark mornings and drunken Decembers. The shoes you wear the rest of the year-round – perforated trainers that let the chill in and low-rise shoes that let the rain in – just won’t cut it in the worst of the weather. You need some of the best winter boots for men and not just one pair, preferably two or three. But how do you go about finding the best winter boots for men? We’re here to help.

Despite those chunky soles and unforgiving leathers, winter boots are some of the most versatile shoes you can buy. Invest in the right pair and they’ll last decades if you look after them as much as they do you. We’ve rounded up fifteen pairs of tried-and-tested, stylish, and ultimately the best winter boots for men that will get you through many chilly winters to come.

Best Duck Boots – L.L. Bean Bean Boots

The word “classic” is defined as “time-tested to be outstanding in quality” and we can think of no word more applicable for the iconic Bean Boot from L.L. Bean. These boots were first crafted in 1911 to be the ideal hunting boot. Fast forward more than a century and there are still few in the ‘best winter boots for men’ category that match their versatility and craftsmanship.

These iconic shoes have it all; the signature rubber bottom half insulates and provides maximum protection from the elements, while the upper is crafted from supple full-grain leather that’s stylish, durable, and timeless even over 100 years after their initial release. One look at the rugged braided sole and you know you have a quality pair of boots on your hands (or feet, rather) and one of the best men’s snow boots around.

One of the most remarkable aspects of the duck boot is its versatility. While designed to protect against snow, puddles, and other elements, these best winter boots for men have become a staple of preppy New England style. Cuffed jeans and a button-down with a cable knit sweater layered over top complete that casual, yet refined look that reads “old money” without being ostentatious.

Best Hiking Boots – Salomon Quest 4D Gore-Tex Forces

Regardless of your outdoorsy aspirations (or lack thereof), hardy hiking boots have established themselves as foul-weather footwear essentials over the past few years. The ideal pair offers untold levels of comfort, ankle support, full-grain leather that only becomes more supple with time and wear, and additional extras like sealed seams and a rugged sole for trudging through both puddles and snow. 

Although hiking boots aren’t typically regarded as fashionable footwear, we have to make a case for the brand Soloman. The Quest 4D Forces offer all of the features you look for in a rugged and tough hiking boot, like the reverse chevron “Contagrip” sole and flexible fit, but in a more modern and stylish package.

To style, team them with other tough-as-old-boots menswear staples like raw denim, corduroy, twill or flannel shirts and cable knit jumpers. You could also pair them with rainstoppers, and fleece to lean fully into the outdoorsy trend. Or be bold and use them as a striking counterpoint to tailoring – just not for your next job interview.

Salmon Hiking Boots, Best Winter Boots for Men

Best Brogue Boots – Church’s McFarlane Highland Grain Brogue Boot

If you’re not ready to go full Bear Grylls with a pair of hiking boots, there are other, subtler ways to infuse your winter look with some outdoorsy influences. A sartorial hybrid, the brogue boot comes with the same reassuring weight and solid construction of hiking boots, but with all the wing-tipped, country-manor smartness of brogues. That clean and classic design easily makes them one of the best choices in terms of stylish best winter boots for men.

Coming in from Church’s, the McFarlane Highland Grain Brogue Boot is the quintessential brogue boot, from its top-notch materials to its traditional decorative brogueing. The hard-wearing highland grain leather, storm welt, and lightweight rubber sole are just a handful of the features these smart shoes possess, all wrapped up in a refined package with just the right amount of country appeal.

As a general rule of thumb, you can wear your brogue boots with any outfit you might normally wear with traditional brogues, so lace up a dark brown or black leather pair with heavier wool suiting, and smart trouser and shirt/cardigan combinations. Don’t be afraid to work in heritage fabrics like corduroy and tweed for added interest either.

Church's Brogue, Best Winter Boots for Men

Best Work Boots – Timberland 6” Waterproof Boots

Some of the best winter boots for men ever made were first designed decades ago for people to wear in factories and shipping yards. The steel toe caps may not have survived the fashion crossover, but many other features have: waterproof materials, padded ankles, high-grip soles, and cozy linings. Why wouldn’t you want those things for your feet when it’s freezing outside?

While the classic Timberland 6” Waterproof Boots have become a staple piece of casual streetwear, this all-season style is ideal for cold temperatures. Besides being waterproof, these boots offer plenty of insulation, a comfortable padded collar, rubber lug sole, and leather from a planet-friendly tannery.

Thanks to the versatility of this style, you can pair them with a range of casual (always casual) outfits, from joggers to jeans, trucker jackets to parkas.

Timberland Classic, Best Winter Boots for Men

Best Combat-Style Boots – Dr. Martens Men’s Work Combat Boots

Like most items in a man’s wardrobe, boots have a proud history of military service. From high lace-ups designed to keep out trench foot to modern tactical designs, combat boots have recorded a number of victories on the fashion front.

When one thinks of the quintessential men’s combat boots, the mind probably goes to Dr. Martens in an instant. Other than their sharp exterior and unique design elements, these boots have one thing going for them in particular: exceptional comfort. The brand’s signature air-cushioned sole and next-level slip resistance will have your feet on cloud nine, even in the frozen hellscape of winter.

When styling a pair of combat boots, one only needs to look at Ryan Gosling’s character in Blade Runner 2049. He paired tactical boots you can buy on Amazon with a statement overcoat. Or designer Charlie Caseley-Hayford who wears his trademark high boots with classic tailoring. Streetwear fans might pair them with jeans and a bomber. Or an easy middle-ground is heritage wear: wool, twill cotton, generous fits, and plenty of herringbone. 

Dr Martens Classic, Best Winter Boots for Men

Best Chelsea Boots – Thursday Boots Duke Chelsea Boots

The Swiss Army Knife of your shoe rack, the Chelsea is by far the most versatile boot you can buy; the right pair looks just as good worn with a suit or tailored trousers Monday to Friday as it does a leather jacket and shredded skinny jeans for a gig at the weekend.

While really any color of Chelsea boot is sure to get plenty of wear this winter, a pair in classic black leather is about as versatile as it gets in terms of footwear. The Duke Chelsea Boots from Thursday Boots checks all the boxes that the best winter boots for men should, with a sleek leather exterior (and interior), studded rubber outsole, water-resistant construction, and the Chelsea boot’s signature elastic goring. Just be sure to have your leather protectant handy to retain that smooth exterior.

When it comes to styling the Chelsea boot, your own sartorial creativity is truly the limit. A long coat, sweater, and chinos makes for a foolproof classic look, while a motorcycle jacket and distressed slim fit jeans will bring the look to the edgier rock-and-roll side of things.

Thursday Chelsea Boots, Best Winter Boots for Men

Best Chukka Boots – Clarks Bushacre 2

As far as we’re concerned, there are few instances in which wearing a pair of desert or chukka boots isn’t a good idea. While their mid-weight construction marks them out as a clear choice for spring and summer, they’re actually a killer option for the winter months, too, along with other ankle tickling styles like jodhpur boots and low-rise hikers.

In terms of footwear, Clarks is to desert boots as Dr. Martens are to combat boots. That is to say that it doesn’t get much better than Clarks’ smart-meets-casual style, complete with a smooth leather exterior (or suede, if you prefer), cushioned insole, and rubber outsole with excellent traction.

With a bit of smart styling, this typically warm-weather shoe can be transitioned to the colder months with ease. Treat this style as a smarter, more hard-wearing alternative to trainers. Team them with chinos, button-down shirts, and crew neck jumpers to create sharp, warm getups that will pass the pub-safe test no problem.

Clarks Chukka, Best Winter Boots for Men

Best Snow Boots – SOREL Caribou Storm Boot

Now we take a turn from the more casual, street style appropriate options and dive into the more rugged options. Think less strolling to the café for a cup of joe and more trudging through the yard to dig your car out of a snowbank. Although the best winter boots for men or best snow boots often find themselves on the more practical side of things, that doesn’t mean you have to disregard aesthetics entirely.

Enter the SOREL Caribou Storm Boot. While we’re not necessarily experts on outdoorsmanship, these classic boots are well known for their conglomeration of comfort, performance, and style that makes them a workhorse if you find yourself six feet under in a snowdrift. These boots adopt a duck boot style with their rubber lower, suede upper, and removable sherpa-lined interior for easy cleaning and added warmth.

Styling these boots can be admittedly challenging. After all, your traditional suiting won’t exactly cut it here. But thanks to the removable liner, these boots can easily be paired with cuffed jeans or chinos, along with cable-knit sweaters and thick flannels. If you need a smarter alternative, a fitted roll neck and blazer combo will do the trick nicely.

Sorel Storm Boot, Best Winter Boots for Men

Best Fur-Lined Boot – Mephisto Leonardo Leather and Shearling Boots

For the coldest and most blustery of winters, sometimes only the coziest and warmest best winter boots for men will do. Whether it’s shearling or faux fur, a bit of fur lining can go a long way in insulating your feet from the sub-zero temperatures.

While classic UGGs have their place, the Leonardo Leather and Shearling Boot offers a much more sophisticated touch. The pebbled leather exterior makes this style easier to care for than a smooth leather option, along with a badass edge that’s right at home at music gigs and bar nights. Add in the shearling lining and cushioned insole and you won’t want these shoes to leave your feet this winter.

To style, you can’t go wrong in teaming these with a well-worn leather jacket and jeans. If you’re going for a more classic approach, the leather jacket can easily be swapped out for a quilted or fur-lined denim jacket.

Mephisto, Best Winter Boots for Men

Best Colorful Option – Taft “The Jack Boot”

In the bleak landscape of winter, a sea of black, tan, gray, and beige often awaits in terms of fashion. While these are all classic colors that do the heavy lifting in terms of closet versatility, some pops of color make for a welcome change to break up the monotony.

The signature style of footwear brand Taft, The Jack Boot, is a classic smart lace-up boot with a twist. While the boot does come in your standard neutral colors, it’s their selection of patterned options that really take the cake here. The Eden Noir pattern is gold floral jacquard that reads “luxe” rather than “grandma’s curtains”. Paired with clean lines, smooth leather, and rubber grips, these boots are an easy way to elevate your winter style.

The best course of action for pulling these boots off is to pair them with a more neutral outfit. Chinos, cable-knit sweaters, and even casual suiting in shades of brown, black, and gray allow these shoes to pop, adding flavor to an otherwise “meh” outfit.

Taft Jack Boot, The Best Winter Boots for Men

Best Jodhpur Boots – Beckett Simonon Douglas Jodhpur Boots

With its smooth leather exterior, characteristic straps, and metal hardware, it’s no secret that the jodhpur boot has its origins in the equestrian world. But even if you don’t plan on becoming the next Triple Crown recipient any time soon, the jodhpur is one of the most attractive and overall best winter boots for men all around.

Crafted from Italian leather and with all of the bells and whistles you could hope for from a smart pair of boots. The elegant exterior of these shoes offers all the clean simplicity of the Chelsea boot but with just the right amount of extra detail to stand apart from the crowd.

The jodhpur boot can transition from the office to the pub with relative ease. Casual suits, chinos, long coats, tweed, and corduroy pair with these just as effortlessly as with jeans, flannels, and sweaters.

Beckett Simonon Jodhpur, Best Winter Boots for Men

Best Sneaker-Style Boots – Red Wing Classic Moc Boot 

It’s always bittersweet when the temperatures begin to drop and our trusty sneakers have to fall out of regular rotation. But even though the Nike and Adidas won’t cut it in the chilly temps, that doesn’t mean you have to completely forgo your beloved sneaks.

Is it possible to have a conversation about the best winter boots for men without mentioning Red Wing Shoes?  Evidently not, because their Classic Moc Boot is easily our pick for this category. With stellar construction and durability, triple stitching, and that iconic contrasting rubber sole, The Moc Boot has remained top of its class since its release in 1952, with a combination of practicality and style that’s just as at home on the streets as it is on the trail.

Thanks to the versatility of this style, you can pair them with a range of casual (always casual) outfits, from joggers to jeans, trucker jackets to parkas.

Red Wing Classic Moc, Best Winter Boots for Men

Best Rain Boots – Hunter Tall Insulated Rain Boots

For every lovely snowy day during the winter, there seem to be five others containing nothing but freezing cold rain, sleet, and puddles galore. Not exactly the weather to wade out in your nicest suede chukkas or recently conditioned brogue boots. But, like an old friend or a rainy day in England, the Wellington boot is something you can always count on.

The brand Hunter needs no introduction. They’ve remained an icon of British fashion for eons and won’t be going anywhere anytime soon. While the classic version of their tall boots may freeze your toes off in a matter of minutes, their insulated version is the ticket to ensuring a frostbite-free winter. This version can be worn in temperatures as low as -5° celsius thanks to an insulated sherpa lining.

There isn’t much to styling your rain boots – a tucked-in pair of jeans, sweater, and army green jacket or trench coat will nicely pick up on the boots’ military lineage. As long as you don’t bring them into your next life-changing meeting, you’re good to go.

Hunter Rainboot, Best Winter Boots for Men

Best High-End Boots – Saint Laurent Lukas 40 Leather Boots

So you’ve got a bit more money to burn on your mission to complete your winter wardrobe; where to begin? In order to get the maximum bang for your buck, you’ll want high-quality material and construction, versatility, and a timeless silhouette that will never go out of style.

In terms of luxury fashion, Saint Laurent is known for its top-notch leather, so you know they’re going to deliver quality boots. The Lukas 40 Leather Boots is the brand’s elegant take on the cowboy boot. The cuban heels add a bit of height while the buttery soft leather and pointed toe cut a sleek silhouette. 

For a look that’s straight out of the pages of a Saint Laurent advertisement, an all-black look will do the trick nicely: black skinny jeans, a sweater, and a biker jacket. And don’t think you have to splurge on your entire outfit to pull these off – the great thing about buying high-end accessories is that they make the entire look seem more expensive in turn.

Lukas Boot, Best Winter Boots for Men

Best Affordable Boots – Golden Fox 6” Boondocker Service Boot

The age-old saying goes that you get what you pay for, but not everyone has a bundle of cash to drop on the finest of the finest. Nevertheless, there are plenty of more affordable options out there that can still play in the big leagues in terms of quality and style.

The Golden Fox Boondocker Service Boots offer just about every perk that’s usually reserved for the higher price tags, with a full-grain leather exterior, steel shank, and Goodyear welt construction that makes resoling easy whenever the need arises, making it a safe addition to the best winter boots for men.

Another plus of this more affordable style is that it can be dressed up or down with just about any combination of winter garb – sweaters, hoodies, coats, jeans, and chinos are all fair game.

Golden Fox Boondocker, Best Winter Boots for Men

How To Choose The Best Winter Boots for Men

Quality Materials

The best winter boots for men shouldn’t be dirt cheap if you want them to last, and you should. “The quickest way to spot quality in a boot is by the quality of the upper material,” says Tim Little, creative director and CEO of Grenson “A well-made boot will always be made of quality leather because no one would go to the effort of making a great boot in cheap leather. Quality leather always has soft creases and usually is hand polished so you can see the patina and dark and light patches. It isn’t always uniform.” Alternatively, look for tanned leather, which tends to be thicker than painted leather and shouldn’t need as much weatherproofing.

Goodyear-Welted Soles

A solid footing in the winter means a pair of the best winter boots for men that feature the famous Goodyear welting technique to stitch the sole firmly to the upper via a rib-like strip of leather or canvas.

“The stitching of the welt can be seen above the welt and the sole stitch (through the welt) underneath the sole,” says James Fox, brand director for Crockett & Jones . “Be careful though. If you cannot see the continuation of this stitch through the sole you could be looking at a pair of cheaper, cemented boots using an imitation welt.”


“A well-made boots brand has detailed information about how they make boots, where they are made and what materials they use,” says Rik Van Dijk from Red Wing . “A good boot maker is proud of this information.” “And if you are looking for a winter boot with the perfect fit and quality? Go to the store of the boot maker or a speciality store. There you get all the information and fit you need to get the perfect boots for your feet.”


Recognizing that most of us only wear the best winter boots for men to either the office or the pub, shoemakers have, in recent years, fitted their designs with comfortable and practical soles. Combat-style treads will make you even more sure-footed while contrast white rubber soles offer some smart-casual hybrid styling.

Likewise, shoemakers (even the likes of Dr Martens) have made efforts to offer lighter versions of their chunkiest and most iconic styles with new materials offering the same wear and practicality.

Although we joke about the dreary awfulness that winter weather brings, it’s not all doom and gloom. The colder months often give us no choice but to put more thought into our wardrobes, which can lead to creating one that fits your lifestyle and personal look best. Any one of these fifteen boot styles will have you on your way to dressing sharper come rain, shine, or (if we must) snow.

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