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Despite popular opinion, the “most wonderful time of the year” is not the holiday season, it’s boot season, and there’s never been a better time to shop for the best boots for men. Boot season opens late summer and lasts until deep into spring, so we’re just starting out here. There’s 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.
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. And while our focus is on fashion, function counts too. You’ll find waterproof — but stylish — rain boots to help you conquer rainy weather.
Here’s how to start shopping for your next pair.
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
BEST 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 initially designed for sportsmen but quickly became a favorite amongst blue-collar workers in factories and farms. For 70 years, this boot has provided the same durability, traction and all-day comfort through high-quality leather 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” because the sturdy leather is a perfect complement to raw, rigid denim. The best 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.
2. Blundstone 500 Chelsea Boot
BEST GARDEN BOOT
Chelsea boots are a do-it-all kind of boot. Surprisingly, few brands are 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 by farmers and other blue-collar workers, like many others listed here.
This boot is incredibly durable, 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.
3. Thorogood American Heritage Moc Toe Work Boots
UNDER THE RADAR
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; Thorogood can continue churning out American-made work boots at an appreciably lower price than Red Wing without the fanfare.
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.
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 initially designed to handle the unforgiving New England terrain and weather that construction workers had to endure regularly. 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.
5. Wolverine 1000 Mile Boot
BEST WORK BOOT
In a previous article, we raved about this boot, 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.
Dress boots don’t necessarily refer to any specific 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 are typically ankle-height, such as Chelsea boots and brogue boots. A solid dress boot will undoubtedly be one of the best boots for men.
1. Thursday Boots Legend Chelsea Boots
BEST OFFICE BOOT
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 the foreground and background at the same time when having them on, which is precisely what you want in terms of office wear. They don’t cost nearly as much as you think, which is great for your bank account. We loved them so much that we named them a favorite for our 2020 Man, and we think they still hold up into 2022.
Pair these with just about anything you wear to work. With these, you will look good no matter what.
SPY MAN AWARD WINNER
2. Beckett Simonon Dowler Boot
Most people would like to pay a fraction of the price for quality goods. Beckett Simonon is one of a handful of new brands 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, high-quality materials and incredible versatility when styling an outfit. They can pack all those into a pair of great boots at a lower, mid-tier price of $239.
It seems too good to be true, but it’s really just a company passing on the savings to the customer. These boots rock; I have a pair myself. Get the Bordeaux color and wear them casually with jeans or dressed up in your autumnal wool suits.
4. Florsheim Lodge Plain Toe Gore Boot
A refined, black leather Chelsea boot is a cornerstone of the modern man’s shoe collection. It looks super smart if you wear it with a pair of jeans, a tee and a flannel or jacket. It also looks super smart if you want to wear it with a blue suit. We think 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.
4. Allen Edmonds Dalton Wingtip Dress Boots
Wingtip dress boots were once prized for their real-world functionality (the brogue detailing proved useful in rainy weather across the pond). Today, they’re sleeker but no less utilitarian. They offer a touch of classic style and serve as a counterpoint to heavier suiting fabrics in the fall and winter. Best of all, when crafted by a revered American footwear brand like Allen Edmonds, they’re about as well-made as possible.
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), the L.L. Bean Boot is an American staple of all-terrain and all-weather footwear. Described as the “antidote to wet feet,” this boot combines a full leather upper with a 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 initially used for hunting but has taken on a much broader role over the years. Many living in the northeast wear these during the wet months to protect themselves from harsh weather, with some wearing 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 rugged pair of jeans and a quilted wool or nylon puffer jacket, maybe from Barbour.
2. Hunter Original Chelsea Boots
Hunter’s Wellington boots are classic, but if you’re looking for something more sophisticated and city-ready, consider their Chelsea boots. 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.
3. Sperry Cold Bay Duck Boots
BEST DUCK BOOTS
Sperry is undoubtedly a go-to option for the best boat shoes and more laidback kicks, but the brand has you covered through more inclement conditions, too. These duck boots are sleek and minimal, as well as performance-minded, featuring a water-resistant build (naturally, of course), plus a padded collar for a comfortable fit. Thinsulate insulation also makes these ideal for cold-weather conditions.
4. Stutterheim Chelsea Rainwalker Boots
Sometimes, functionality tops style points, especially when staying dry in a downpour. Thanks to European footwear masters Stutterheim, you get the best of both worlds by using these sleek-yet-utilitarian rubber Chelsea boots. The black color doesn’t miss a beat as you dress for your commute and the office.
5. XTRATUF Deck Boots
BEST FOR BAD WEATHER
Of course, every guy needs a pair or two of the best boots for men. But what about boots that are suitable for work and the elements? The stakes have been raised even further, but there’s an easy way to meet both demanding circumstances: Get these rugged, hard-wearing XTRATUF boots, which have been trusted by hard-working crews on boats traversing the frigid waters of Alaska (and elsewhere, of course). These are extremely grippy and 100% waterproof.
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 stylish casualwear staple. If you’re not sure about this trend, don’t worry; brands like Tecovas make western boots that are surprisingly city-friendly.
1. RM Williams Comfort Craftsman Boot
America may be where cowboys were born, but their spirit endures in Australia. These boots come from R.M. Williams, an Aussie brand that’s been making boots for riding since the 1930s. The Comfort Craftsman is a slightly elevated take on both the Chelsea and the cowboy boot, and while these boots are expensive, they’re painstakingly crafted in Australia and built to last.
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 an urban slant and brought it to something wilder: cowboy boots. These zip boots have a Western-inspired silhouette but are still sharp enough to wear in the city.
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 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.
4. Rhodes Footwear Roper Boot Caliber
Roper boots are among the more authentic styles of Western boots, designed for plenty of hard-working time on the ranch yet also hitting what Huckberry calls the “sweet spot” between Cowboy boots and dress boots. That makes them versatile and well-suited to team with denim or canvas chore pants. It helps that the waxed cowhide upper is long-lasting and will only get better with age.
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. Eddie Bauer K-6 Boot
Hiking boots may have come a long way in terms of performance and features since this style of boot reigned supreme, but there’s something especially stylish about old-school hiking boots that we’ve been feeling lately. Eddie Bauer’s K-6 boot looks similar to the iconic Danner hiking boot at a much more affordable price. You’re still getting a great boot; the K-6 boasts a Vibram sole and a breathable but water-resistant leather upper.
2. Keen Pyrenees Hiking Boots
Keen has a knack for blending the best of the old and the best of the new, which is probably why the brand’s Pyrenees Boots are a favorite. Here, they’ve used a proprietary Keen Dry membrane for waterproof protection, and the waterproof nubuck leather upper is durable and dependable when conditions take a turn for the worse out on the trail.
3. Season Three The Ultralight Hiking Boot
BEST FASHION HIKER
Season Three is a newer brand that should be on your radar. The young upstart out of Brooklyn has made serious waves in the world of boots, 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.
4. Merrell Moab II Mid Hiking Boots
The competition is fierce when finding the most technical hiking boots on the market, but Merrell might have just taken the cake with its ever-popular Moab II Mid Hiking Boots. They blend a breathable mesh lining and waterproof exterior with hard-working features like a protective toe cap (useful on rocky trails), and the traction-focused Vibram rubber sole offers plenty of grip, no matter how tough the going gets out there.
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, as long as it’s not snowing or raining, of course. 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 completely rocked British and American boot culture back in 1950. Nathan Clark created his famous desert boot after drawing inspiration from the off-duty boots worn by army officers 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.
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 generally go for less than $200. If Clarks isn’t nervous, they should be.
3. Clarks Wallabee Boot Maple Suede
Compared to the classic and refined desert boot, the Clarks Wallabee is 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.
4. Todd Snyder Nomad Chukka Boots
The all-American design ethos of Todd Snyder shines through in the company’s first-ever pair of Todd Snyder-designed boots. These have all the classic hallmarks of timeless chukka boots, from the rubber sole to the handsome suede upper. Pair them with Todd Snyder selvedge denim and a crisp Oxford shirt for a style that can go anywhere this fall.
5. Barbour Redhead Chukka Boots
BEST ROAD TRIP
Barbour is famous for crafting some of the best men’s jackets for the open road, if not the best on the market, and they’ve translated that same care and attention to detail into a pair of finely made chukka boots too. These are fit for work or play and fall road trips aplenty, and it’s helpful that the rich suede is well-suited to fall and winter looks, too. The rubber sole provides grip on slick streets, while the profile is dressy yet versatile.
Much like sneakers, combat boots that were once at the forefront (or the front lines) are now better-suited to fashion than their original purpose. And that’s okay because you can wear these stylish boots without being mistaken for a paratrooper. That’s not to say you can’t wear more tactical styles, so long as you style them correctly (maybe skip the camo pants to avoid stolen valor).
1. 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 of April in 1960, was initially sold as the go-to work-wear shoe for mail carriers and factory workers. It wasn’t 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 almost any color imaginable, but the most popular will always be black. They may have technically originated as work boots, but their appeal as a combat boot is undeniable.
2. NORTIV 8 Men’s Military Work Boots
Nortiv 8 is a brand that makes tactical boots and work boots, and though we’ve yet to try a pair ourselves, they’re backed by solid reviews online. They’re economical, and they have a decidedly tactical look. They’re available in tall and low-cut styles.
3. Camper Brutus
Camper’s shoes are subversions of the classics, and these Brutus boots are a perfectly streamlined take on a combat boot. They have a thick rubber lug sole and an upper cut from leather, with OrthoLite insoles for cushioning and comfort. They’re lace-ups, but they have a zip on the side to easily put them on and take them off.
4. Naglev Combat WP Boots
Naglev’s boots combine the comfortable as sneakers with all the rugged appeal of lace-up boots and all the performance features of hiking boots, complete with a Kevlar outer shell, speed lacing and a natural rubber outsole for good measure. They’re part hiker, part combat boot and all style.