The Best Men’s Boots in 2022: Our Icons and Must-Knows

best boots
Courtesy of Thursday Boots

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Despite popular opinion, the “most wonderful time of the year” is not the holiday season, it’s boot season. Boot season opens up late summer and lasts until deep into spring, so we’re just getting started out here. While we recently welcomed back flannel, layering and our favorite pairs of jeans a few months back, we’ve been rocking boots ever since the weather dipped below 70 degrees. There’s just no better feeling than opening up, smelling (trust us on this) and slipping on a new pair of leather boots to celebrate the changing season.

The best men’s boots can hold the weight of being the centerpiece of your cold-weather wardrobe. They turn good outfits into great outfits and, if styled well, can make you look really smartistic (smart + artistic; credit: me, who is wearing boots right now). But the truth is that boots know no boundaries, and every unique type of style has at least one boot to match.

Seasoned boot wearers may be keen on the ins and outs of what looks good, but for newbies, finding a good pair of boots for men can be very overwhelming. That’s especially true once you get into details like cap-toe vs. moc toe and wedge sole vs Cuban heel. That’s why we’ve rounded up the best boots for men by broad category, including dress boots and work boots, which are always in style, plus timeless picks that happen to be trendy, such as hiking boots and western boots. That way, you can easily find what works for you and maybe pick up one of each (or all of them, treat yourself).

Here’s how to start shopping for your next pair.


Dress Boots

Dress boots don’t necessarily refer to any one specific kind of shoe, but this broad category refers to shoes that can be worn in an office setting, and in some cases, with a suit. They’re generally leather, rather than more casual suede, and they’re typically ankle-height, such as Chelsea boots and brogue boots.


1. Thursday Boots Legend Chelsea Boots


Back in the office? Whether you are or aren’t, these are the boots to have on when strutting from your desk to the bathroom. The matte black color is a subtle flex that keeps you in both the foreground and background at the exact same time when having them on, which is exactly what you want in terms of office wear. They don’t cost nearly as much as you might think, either, which is great for your bank account. We loved them so much, we named them a favorite for our 2020 Man.

Pair these with just about anything you wear to work. With these, you will look good no matter what.

Thursday Boots Legend Chelsea Boots, best men's boots Courtesy of Thursday Boots


2. Beckett Simonon Dowler Boot


Most people would like to pay a fraction of the price for quality goods if they can. Beckett Simonon is one of a handful of new brands that are making that happen in the shoe department. The Dowler boot from Beckett Simonon was previously ranked as one of the best dress shoes for men by SPY because of their attention to detail, use of high-quality materials and incredible versatility when styling an outfit. They’re able to pack all those into a pair of incredible boots at a lower, mid-tier price of $239.

It seems too good to be true but it’s really just better company operations passing on the savings to us, the customer. These boots rock, I have a pair myself. Get the Bordeaux color, you’ll be glad you did, and wear them both casually with jeans or dressed up in your autumnal wool suits.

Beckett-SImonon-Dowler-Boot Courtesy of Beckett Simonon


3. Grenson Fred Leather Brogue Boots


Even with stiff competition stateside and in places like Australia, British bootmaking still continues to shine. From Tricker’s to John Lobb to George Cleverly to Church’s, there are almost too many great British footwear brands to name. Grenson is another name in that venerated list, and these lace-up boots combine a thick rubber sole with a brogued upper to create a shoe that’s rugged yet sophisticated.

boots Image Courtesy of Mr Porter

4. Florsheim Lodge Plain Toe Gore Boot


A refined, black leather Chelsea boot is a cornerstone of the modern man’s shoe collection. If you want to wear it with a pair of jeans, a tee and a flannel or jacket, it looks super smart. If you want to wear it with a blue suit, it also looks super smart. In our opinion, Florsheim’s upped their style game and created a smartly styled option for the Chelsea boot. One of the loudest gripes about Chelsea boots is that the circumference of the opening is too narrow for the foot to easily slide inside, but Florsheim widened the boot’s throat, making wrestling with your boot a thing of the past. There’s more sleekly styled comfort with this boot, the toe is a rounded almond shape, meaning your toes won’t get cramped like they do in pointy-toed boots. Inside is an OrthoLite cushioned footbed that absorbs shock while providing support and comfort. Don’t like a black boot? Well, it also comes in two different shades of brown.

Florsheim-Lodge-Plain-Toe-Gore-Boot Courtesy of Florsheim


5. TAFT Jack Boot


TAFT may be one of the hottest footwear brands born online as of late. With a cult following, TAFT has popped up as one of the new leading faces in the world of boots, but also sneakers and dress shoes. The TAFT Jack Boot, in particular, is one of the styles that put the brand on the map. It’s the perfect combination of minimal and interesting while providing a near-perfect flex player between dressing up and dressing down an outfit. The use of raw wool for the upper with a sturdy leather cap toe and heel counter are the king of compliments when it’s on foot. With more than a whopping 1,100 reviews and a consistent five-star rating, you know this has to be one of the best men’s boots for fall. Grab it in your favorite color-way, including navy with brown, grey with black, plaid with brown, among other options.

Taft Jack Boot Image courtesy of Taft


Work Boots

Work boots are pretty much what they sound like — boots for working in. Though brands like Red Wing and Timberland made shoes for laborers, these shoes have since evolved into lifestyle shoes that you can wear casually. That’s not to say they’re less hardwearing; many of the best work boots are still Goodyear-welted and made with waterproof uppers.


1. Red Wing 6” Moc Toe


Red Wing’s 6” Moc Toe boot is the most iconic moc toe boot for men. Released in the 1950s, this moc toe boot was originally designed for sportsmen but quickly became a favorite amongst blue-collar workers in factories and on farms. For 70 years, this boot has provided the same exact durability, traction and all-day comfort through high-quality leathers and excellent design. Aside from the moc toe, this boot is easily recognizable thanks to its chunky Traction Tred rubber sole.

Today, the Red Wing 6” Moc Toe boot has become one of the most popular lifestyle boots. They’re basically attached to the feet of “denim heads,” or people who have a denim-first wardrobe because the sturdy leather is a perfect compliment to raw, rigid denim. The best type of look for this boot is that pseudo-lumberjack vibe with a pair of cuffed-up slim-fit jeans, a clean white t-shirt, and a denim jacket. Note: Order a half to a full size down.

Red Wing 6” Moc Toe Courtesy of Zappos


2. Blundstone 500 Chelsea Boot


Chelsea boots are a do-it-all kind of boot. Surprisingly, not many brands are actually well-known in mainstream American shoe culture for making a Chelsea boot. Blundstone, boasting over 150 in the footwear game, takes exception to that with the original 500 series. Blundstone’s 500 Chelsea Boot hails from the 1960s and was originally used, like many others listed here, by farmers and other blue-collar workers.

This boot is incredibly durable, made with weatherproof oiled leather, a slip-resistant sole and shock-absorbing technology in the midsole. Whether you’re somebody who has to traverse the cobblestones of New York or just likes to look cool in rugged gear, this Chelsea boot is sure to do the trick this year.

Blundstone-BL500, best men's boots Image courtesy of Zappos


3. Thorogood American Heritage Moc Toe Work Boots


Red Wing is so storied and beloved that Thorogood tends to get overlooked, even though the latter was founded over a decade before Red Wing. But maybe that’s for the best; without the fanfare, Thorogood can continue churning out American-made work boots at an appreciably lower price than Red Wing. Their 6″ moc toe is sturdy, stylish and well built, and the wedge sole provides slip resistance. The uppers are made from oil-tanned full-grain leather, the fiberglass shank provides structure, and the Goodyear storm-welted soles provide long-lasting performance. Plus, a Goodyear welt means these shoes can be re-soled once the rubber wears down.

boots Image Courtesy of Amazon

4. Timberland 6” Premium Waterproof Boot


This boot may be one of the most iconic in modern times. The Timberland 6” Premium Waterproof Boot was originally designed to handle the unforgiving New England terrain and weather that construction workers had to regularly endure. And it worked! Since 1973, the boot’s waterproof, seam-sealed Horween leather design has blocked out splashing from puddles or rain while the durable rubber outsole has provided as much offense on the ground as it does defense for the foot inside it.

What Timberland didn’t see coming was the massive impact this style would have on hip-hop culture a couple of decades later. The ’90s saw legendary artists like The Notorious B.I.G and Tupac Shakur. Today, the Timberland 6” Boot has been spotted on the likes of Rhianna, Kanye West and athletes by the hundreds. Wear this staple boot with your favorite jeans, whether loose or skinny and a plaid flannel shirt or jacket this fall.

Timberland-6-Inch-Premium-Waterproof-Boot, best men's boots Image courtesy of Zappos


5. Wolverine 1000 Mile Boot


We raved about this boot in a previous article, but Wolverine’s 1000 Mile Boot is the real deal. Described by Wolverine as “America’s Original Workboot,” the 1000 Mile Boot of today is a recreation of the original design from 1914 that sought to provide both comfort and toughness to the grueling daily life of the average working man. This boot is still 100% produced in the United States.

The leather upper is made from Chicago-produced Horween Leather, the classic leather sole and Vibram rubber heel from Williamsport, Pennsylvania and the flat waxed cotton laces are made in Landrum, South Carolina. The most popular color in this boot is brown, but many colors are available today. Choose your pair wisely, because chances are they’ll outlive you.

Wolverine 1000 Mile Boot, best men's boots Courtesy of Zappos


6. Dr. Martens 1460


Like the Clarks Desert Boot, you’ll know Dr. Martens’ 1460 as soon as you see it. This boot is easily recognized by the translucent Dr. Martens air-cushioned sole and iconic yellow welt stitching. The 1460, which was officially released on the first day (1) of April (4) in 1960 (60), was originally sold as the go-to work-wear shoe for postmen and factory workers. It didn’t take long before the style was adopted by the rebels of Britain’s underground music scene, including the infamous Pete Townshend of The Who.

Since then, the Dr. Marten 1460 has become an international symbol of individualism, going against the grain of society, and most certainly, comfort. You can find the 1460 in just about any color imaginable, but the most popular will always be black. Style your Doc’s with anything you feel like putting on, because these boots mean not giving a flying f*** about what society, your mom or anyone else thinks about your clothes. Do wear socks, though — trust me.

Dr. Martens 1460 , best men's boots Image courtesy of Zappos


7. Frye Harness 12R


That’s right, best for riding things. Here’s the story. New England neighbor to L.L. Bean, the Frye Boot Company dates back to 1860’s Massachusetts. Their boots were worn by soldiers on both sides of the Civil War and by the American cavalry during the Spanish-American War, including a young Teddy Roosevelt and the Rough Riders. Flash forward to the 1970s, the Frye Harness 12R boot was released as a tribute to these military riding boots and given a detailed upgrade with the metal ring harness around the ankle. While most people in the ’70s weren’t on horseback, motorcycle culture adopted these as the go-to boot to keep them safe. In fact, one review on the company’s website even says their boot saved them from being severely injured in a minor crash. Whether riding horses or a motorcycle, these boots go best with denim and other leather garments. Try it with black jeans and a thick leather jacket, maybe from Schott NY.

Frye-Harness-12R Image courtesy of The Frye Boot Co.


Rain Boots

You might not get to wear them year-round, but rain boots are a closet essential for keeping your toes dry when it does rain. Many rain boots are made from rubber, which, while not as durable or comfortable as leather, does a better job of staying dry. Some boots, like the LL Bean duck boot, combine the benefits of leather and rubber.


1. L.L. Bean Boots


Made in Maine for over an astounding 100 years (since 1912), theL.L. Bean Boot is a New England, and arguably an American, staple for all-terrain and all-weather footwear. Described as the “antidote to wet feet,” this boot combines a full leather upper with a completely waterproof rubber sole that boasts some of the best damn traction you’ve ever seen. The “Bean Boot,” designed by L.L. himself in 1911, was originally used for hunting but has taken on a much more broad role over the years. Many living in the northeast wear these during the wet months to protect themselves from harsh weather, with some having worn the style since childhood. The Bean Boot is also commonly found as the boot of choice on college campuses! Wear this boot in the fall with a tough pair of jeans and a quilted wool or nylon puffer jacket, maybe from Barbour.

8-Inch-L.L.-Bean-Boots, best men's boots Image courtesy of L.L. Bean


2. Hunter Original Refined Chelsea Boots


Hunter’s Wellington boots are classic, but if you’re looking for something more sophisticated and city-ready, consider their Chelsea boots (which have refined right in the name). They’re inspired by classic leather boots, but they’re made from vulcanized rubber with an elastic gusset. Because of the permeability of the elastic, these boots are best suited for walking on streets, rather than trudging through mud or hopping in puddles.

boots hunter Image Courtesy of Zappos

3. Bottega Veneta Green Puddle Boots


Every time it rains, you see a sea of Bean boots and Hunter Wellingtons. If you want your wet weather footwear to stand out, Bottega’s puddle boots are the shoes for you. They come in a unique shade of green and have a chunky silhouette with a pronounced sole. These lightweight boots are 100% rubber and are made in Italy.

boots Image Courtesy of SSENSE

Western Boots

From Red Dead Redemption to RRL, Americana and the wild west have proven to have an enduring staying power in pop culture. And it’s not just denim jackets and pearl-snap shirts; cowboy boots have become a surprisingly stylish casualwear staple. If you’re not sure about this trend, don’t worry; brands like Frye and Tecovas make western boots that are surprisingly city-friendly.


1. Frye Grady Chelsea


If you want to inject some wild west energy into your footwear rotation without going full caballero, Frye’s Grady boots are the pair to buy. Frye was founded in 1863, making it one of the oldest footwear brands in America. The pointed toe and a medallion design on the upper bring a cowboy boot inspiration, while the ankle cut, elasticated gusset and refined leather construction bring some British Chelsea boot inspiration.

boots Image Courtesy of Frye

2. Tecovas The Roy


When you imagine direct-to-consumer disruptors, you’re most likely thinking of markets like eyewear, furniture and casual clothes. But Tecovas took the DTC ethos, which has typically had something of an urban slant and brought it to something a little wilder: cowboy boots. These zip boots have a western-inspired silhouette but are still sharp enough to wear in the city.

boots Image Courtesy of Tecovas

3. Ariat Rambler Boot


The Rambler is the do-all western boot for guys, and that can also include just looking great and feeling great, thanks to the cushioned insole, on a day-to-day basis. If you’re new to the western look, the Rambler boot shaft is an ideal height for all guys and perfect for tucking in pants or otherwise. Match it back with any wash of blue slim or bootcut denim, a trusty ol’ white t-shirt and a lightweight button-up. Bonus points if it’s a dual chest pocket western button-up.

Ariat-Rambler-Boot Image courtesy of Ariat


Hiking Boots

Along with western boots, hiking boots have firmly stepped out of the world of the outdoors to become surprisingly stylish everyday boots. You can wear them with technical or rugged clothing, but they look just as good with a pair of corduroy pants and even some dress pants.


1. Danner Light Mountain Boot


Hiking boots may have come a long way in terms of performance and features since Danner first introduced its hiking boots, but in terms of style, Danner’s iconic Mountain boot is unparalleled. These boots have traditional hiking laces in contrasting red, and the sole is durable Vibram. Danner’s boots are also made in the US. Stock is pretty limited at the moment, so if you see them in your size, it’s not a bad idea to pick them up now.

boots Image Courtesy of Todd Snyder

2. Sorel Mac Hill Waterproof Boot


Any time it’s cold, you’re sure to see men, women and children strutting around in Sorel. The Mac Hill is a more street-ready boot that draws inspiration from hiking boots and sneakers. The leather upper is waterproof. The removable insoles and supportive rubber soles ensure comfort for long days on your feet. Plus, they’re stylish enough to work in a variety of settings.

boots Image Courtesy of Nordstrom

3. Season Three The Ultralight Hiking Boot


If you don’t know about Season Three, it’s time you learned. The young upstart out of Brooklyn has made serious waves in the world of boots, and it’s all thanks to their surprisingly light, incredibly durable Ultralight Hiking boot. Available in a range of colors, this city/trail hybrid boot will keep you looking fresh whether you’re walking down the street for a cup of coffee, grabbing drinks with friends, or traversing local trails on the weekend.

best hiking boots - season three Season Three

4. Merrell Moab Mid 2 Waterproof Boot


The Merrell Moab Mid 2 hiking boot is part of the “Mother of All Boots” collection, which is an accurate descriptor for this do-it-all boot. This waterproof version of the Moab 2 boot is perfect for the uncertain outdoor conditions that fall may bring in certain regions of the country. In other words, it keeps you on your toes when treading terrain turns treacherous.

Whether your trail crosses water, scrambles across ridges or simply requires a boot defensive enough to unwaveringly step on rocks, this technically-designed boot can handle it. If you go with this as your hiking boot, you’ll find solace in the ample ankle padding and support.

Merrell-Moab-Mid-2-Waterproof-Boot Image courtesy of Zappos


5. MONTELLIANA 1965  Waxed Canvas Hiking Boots


Montelliana 1965 is a fairly low-key and unknown brand despite the fact that they were founded, as the name suggests, in Italy in 1965. But that just means you’re more likely to get questions about where you got your boots from, especially when they look this unique. These hiking boots are made from a blue waxed canvas, rather than the traditional leather, and the contrasting rubber sole, leather panels and bright green laces make these boots stand out even more.

boots for men montelliana Image Courtesy of Bloomingdales

Chukka Boots

Chukka and desert boots sit low on the ankle and are often made from breathable, soft leathers like suede. These make them great year-round boots; you can wear them in summer with a breathable cotton chino or in winter with a sturdy pair of cords. Unsurprisingly, Clarks is the name of the game here, but there are other boot brands to know.


1. Clarks Desert Boot


The Clarks Desert boot is not only the most iconic Chukka boot, but it completely rocked British and American boot culture back in 1950. Nathan Clark created his famous desert boot after drawing inspiration from the boots off-duty worn by army officers while stationed in Cairo and Burma through World War II. The Clarks desert boot is a staple casual boot and is distinctly identified by its crepe sole, made from coagulated latex. What that means is that these shoes are very comfortable from day one.

a pair of Clarks Desert Boots Image courtesy of Zappos

2. Astorflex Greenflex


Astroflex boots have been made in Italy for a long time to exacting standards. The soles are made from 100% natural rubber, and the premium leather is aged for 30 days in an environmentally-conscious way. Plus, these boots look damn good, and they generally go for less than $200. If Clarks isn’t nervous, they should be.

boots astroflex Image Courtesy of Huckberry

3. Clarks Wallabee Boot Maple Suede


Compared to the classic and refined desert boot, the Clarks Wallabee is something of a wild child. It’s a little weirder, a little uglier and for those reasons, a little cooler. Wu-Tang Clan undeniably made the Wallabee their own, and the shoe has since been sported by rappers ranging from Kanye West and Drake to Nas and Slick Rick. And since these shoes sit on a cushioned crepe sole with uppers of supple suede, your feet are sure to be comfortable all day.

boots Image Courtesy of Clarks

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