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Informed by hands-on testing, our guide to the best boots for men covers nearly every category, from work boots to Chelseas, chukkas and more. Curtain Grommet Machine
Boots always seem to get more done than shoes. While shoes are busy arguing semantics in a boardroom, boots are out in the garage actually doing work. Shoes spend their weekend shanking golf balls while boots are going over, around and through every surface on Earth. Boots have long belonged to the movers and shakers of history, and I'll be damned if that isn't about everyone. No matter whether you're wandering out into the woods to do "real" work or simply walking yourself around the corner for a coffee, boots guarantee you'll get there.
But "boots" is a broad category. There are Chelsea boots, rain boots, snow boots, cowboy and desert boots, too, but also a dozen more. Be warned, this guide not only delves into the best picks from each of these pillar categories but also serves as a broader breakdown of the best brands. These are the places you should be buying your boots from. Why? Because we've tested enough boots to know there's a serious gap between good and bad, what won't do the trick and what will survive a wet-season hike (hint: hiking boots). But there are loads more boot types to know — and buy. Find them below.
Ankle boots might be the coolest footwear ever made — which makes them that much more difficult to pull off than their closest cousins, the Chelsea boot. They’ve graced the feet of rock stars and, in doing so, complemented the tightest pants mankind has had to offer for decades.
The silhouette is similar to the Chelsea boot, but the Ankle boot utilizes zippers or straps instead of elastic panels to ensure a secure fit around the ankle. A common style of ankle boot is the strappy, geometric Jodhpur boot, and side-zip boots with a streamlined profile also complement edgy, slim pants favored by counterculture heroes.
Chelsea boots began life in England in the mid-19th century and didn’t stray far from home until recently. The elasticized wonders were a staple of the mid-’60s mod scene and protected the feet of seemingly every British invader from John to Ringo. Recently they’ve seen a revival on many of menswear’s best dressed, including guys like Chris Evans and Ryan Reynolds. Fear not, though: It’s a style you can rock just as easily. The silhouette is very slim and features elastic side panels and heel pull-tabs.
About as casual as all-leather boots get, the chukka (or desert) boot was first worn by British soldiers in Africa during World War II. Afterward, they made their way across the Atlantic, becoming a casual staple for the second half of the 20th century and still gracing the feet of stylish men in the cooler months. They were a particular favorite among prepsters, who paired the style with chinos, and today’s offerings work just as well with modern stretch pants as with expertly faded denim.
Clarks made the originals, but upmarket offerings only improved on the formula. They lace up just above the ankle and traditionally feature a soft crepe sole.
Combat boots are, well, boots typically worn by those in active combat. As with other military essentials turned civilian staples (like the field jacket or the cotton twill chino), they eventually made their way into daily life. Brands like Dr. Martens were adopted by everyone from punks to beatniks, and if you look closely, you’ll find the style never really went away.
In the fashion world, they're a rugged boot with a rubber sole, and a chunky one at that.
Like many Americana wardrobe staples, cowboy boots are rooted in function. Pull them on, wear them hard and use them for years. There are two main styles: traditional cowboy boots that feature a riding heel (taller and angled) and roper boots that have a shorter heel, designed to handle a day of walking.
The pointed toe and tall shaft make this boot instantly recognizable. In recent years, cowboy boots have picked up serious steam as consumers gravitate toward all things “Western,” from denim shirts to cowboy hats.
Popularized by L.L. Bean, the Duck boot style features a waterproof bottom with a high shaft. The collar usually ties pretty tight to create a similar seal and the toe harks back to a duck's bill. There’s a reason L.L. Bean’s “Bean Boot” usually has a waitlist: They’re a highly functional original, but plenty of other brands make their own duck boots, too.
The original Engineer boots were designed to protect the feet of men who fed coals into steam engines. It melded the tall pull-on style of horse riding boots with the supportive arch and sole of a work boot. A buckled ankle strap distinguishes this style from other pull-on boots.
Engineer boots are less common in the world of men’s boots at large, but the style calls to mind a rugged heritage and can pair nicely with workwear and indigo denim.
For the purposes of this guide, we’ve kept a respectful distance from the more technical versions of this style, but the best pairs of old-school hiking boots boast the same alpine prowess that made them popular in the first place. Sturdy soles, heel support and lace-to-toe closures mean these boots are as hardworking as they are good-looking.
Today’s hiking boots are occasionally made from traditional leather with waterproof functionality, but you’ll also find hiking boots made with modern mesh fabric and sneaker-like soles.
For actual hunting, you may want something more technically advanced, but the hunting boot is a staple in the Northeast and has ensconced the feet of everyone from frat boys to Nobel prize winners. The traditional style features a hand-sewn moc-toe, a lace-up closure and a durable, grippy outsole.
It should come as no surprise that some of the best makers of old-school hunting boots (like Rancourt and Quoddy) are also based in the Northeast.
While you could wear whatever boots you want in the rain, a dedicated rain boot will keep your feet dry — and you on your feet, too. Rain boots feature waterproof uppers, better tread and a quick-drying inside in case you do get wet. They're usually pretty tall, too.
The best rain boots are usually built atop a sturdy rubber sole for intense traction, and some styles feature pull-on (not lace-up) construction.
Sure, certain Duck or Chelsea boots work in the snow, but, like rain boots, a dedicated design built for snowfall is smarter. Snow boots feature waterproof uppers, chunky soles, better tread and some sort of membrane to keep your toes dry (and warm), which means there's usually insulation within.
Popular types of insulation include Gore-Tex, although some might feature a shearling collar or lining for added warmth. Look for pairs with a taller lace-up shaft for maximum coverage.
Worn since World War I, the trench boot (sometimes called an army or officer boot) is a handsome staple that’s shaken its military roots and manages to look a bit more cleaned up these days than it did stomping into Flanders. Similar to the work boot, this silhouette has a lower profile that is easier to incorporate into a variety of wardrobes.
Trench boots are often made of rich leather (sometimes from a U.S. company like Horween), and they feature a slightly taller lace-up shaft. Your trench boots will undoubtedly look even better with age.
Work boots are meant to be tough but not all work boots are waterproof. Waterproof work boots in this category can both withstand dirty jobs and keep a seal in puddles and ponds. (Just don't go into waters taller than the boots are.)
Work boots are seam-sealed and sometimes made with reinforced details like a rubberized leather toe or heel cap. The collar is often thicker and padded for comfort, and the toe is bulky and rugged with a wider toe box.
The wingtip, whose brogued details bring a touch of formal embellishment to casual footwear, is dressed up enough to be worn with a suit and laid back enough to end up under denim or a pair of cords. The first wingtip boots were created specifically to take on marshy, peaty bogs, and they’re still a casually rugged style with functional history. Don’t just call them a mullet shoe: they’ve been around long enough to look equally good in either context.
Strong, long-lasting and just stylish enough to stay on your feet for most of the colder months: that’s all a work boot really needs to be. Little wonder that the design was more or less perfected half a century ago. The no-frills lace-up style protects the lower legs and feet and usually features a durable lug sole.
Materials like weather-resistant leather bolster the utility of these boots. Some styles even feature reinforced canvas inserts throughout the upper for added durability.
According to Jay Carroll, co-founder of Wonder Valley and El Rey Court and former Levi's concept designer, the best boots are those closely attached to your way of life.
"When I'm out West in Joshua Tree," he says, "I love my roughout suede cowboy style boots I had custom-made in Texas. They fit like a glove and I live in them. They can get real dusty while kinda dressing up a bit everything I wear with them. I find this style incredibly timeless."
Being bi-coastal, though, he needs an alternative that can withstand the East Coast elements, too. "When I'm on the coast of Maine and on the water a lot I wear these minimal pull-on deck boots. I have them in capers and in white. I can wear them on the dock and on the boat but also wear to town. For my life out East I find them to be very versatile."
Boots with a story to tell, with genuine performance and style built in, remain vitally important in the market at large, said Oliver Gilbertson, the global design director of Cat Footwear.
"Authentic brands continue to be valued by consumers," Gilbertson says, noting that workwear and work boots have a steadfast position in the market. Gilbertson notes that hiking boots and cleanly designed Chelsea boots are gaining ground, too.
"Consumers are looking for greater functionality from these silhouettes with clearly visible features, materials, constructions, and details that address seasonal weather conditions and testing terrains," Gilbertson says, pointing to features like waterproof and even salt-resistant leather for fall and winter.
"Simple classic boot styles never go away but greater, visible functionality will become more and more important," Gilbertson says.
Celebrity men's stylist Vanessa Powell makes prescriptive decisions for men every day and has her own opinions on which boots are trending right now.
"Right now, I'm loving the chunky Chelsea boot style for men. Chelsea boots are a closet staple, but the added lug make this classic more hip to the streetwear trends. Plus, they are all-weather friendly so you can tackle the elements in style," she says. If you don't love slip-on boots, she says, find a pair you can tie tightly (but still have a sizable outsole). "You can never go wrong with a leather lace-up pair of boots," she explains. "They are not as edgy as a combat, or rugged as a work boot, and can be dressed down for daytime with denim and up for a night out with chinos. The best are ones that look like a dress boot that have a functional tread."
We've highlighted the brands we recommend and the models from there we like, leaving you with the tools to make an informed purchase. But remember, always check the sizing standards for your chosen brand before ordering.
For a guide to how most major brands' shoes fit, follow our guide to men's shoe sizes.
After compiling a list of the best widely available boot brands, we picked the most quintessential model from each label. Using this shortlist as a guide, we began testing as many models as we could reasonably wear in the fall and winter months. We considered how and where the boots were made, how they looked and felt on, as well as how they looked and felt after their fair share of wears.
The below products not only represent the best styles from each brand but a number of boot categories, too — from duck to work boots to cowboy boots, and back again. This list will continue to grow as brands emerge and old ones debut new designs.
To learn more about our testing methodology and how we evaluate products, head here.
Rhodes is a brand owned and stocked exclusively by Huckberry. All of the boots are made in Léon, Mexico, the country's boot capital, from leather uppers and lightweight Meramec PU outsoles, which prove slip resistant and ultra-soft. Albeit new, the brand's establishing itself as a go-to purveyor of polished, long-lasting boots.
Rhodes' Tyler Chukka combines full-grain roughout uppers and a soft, crepe-like outsole. The pairing promises comfort, a refined yet casual look and enduring quality, a trifecta few brands truly deliver on.
Although the company's true timeline proves vague, Astorflex has been around since the 19th century. Maybe it's one of those mysteries brands within the spirits industry typically upholds: "oh, well, we were founded first in 18xx, stopped making product in 1903, and then were relaunched by investors in 2021. we're 200-years-old!" The brand started out making wooden clogs but its online catalog now includes everything from Chukka boots and mules to sneakers and Chelseas.
Astorflex is something of a revelation, making fairly priced boots in timeless styles using eco-friendly materials. The Brownflex Chukka Boots bring it all together, updating a fan-favorite Astorflex silhouette with a full leather lining for added comfort. The boot also still rests atop a durable yet springy crepe rubber sole.
There's a little tidbit of footwear history I always get wrong: where was Alden founded? I want to say England. Makes sense, right? It's New England, for those wondering what the right answer is. The family-owned company's footwear has been made in Middleborough, Massachusetts since 1970, in a factory they relocated to after sharing one with Old Colony Footwear for decades.
The Alden Indy Boot earned its name by way of being the choice shoe of fictional professor of archaeology, Indiana Jones. These are cut from suede and finished with the famous orthopedically correct lasts, and you can even find them at J. Crew occasionally.
Boots aren't all menswear brand Taylor Stitch makes. They have everything from jackets and shirts to trousers and sunglasses are up for grabs on its site. Each of Taylor Stitch's products is united by a shared concern for craftsmanship, evident by high-quality construction at a transparent cost. The boots, made by hand in Léon, Mexico, the country's shoemaking capital, are meant to last.
Taylor Sitch's Moto Boot may be stylish but makes for a great all-around work boot, too. Crafted in Léon, Mexico, it uses triple-needle stitching and Goodyear storm welt construction for longevity. It's made with durable yet soft weatherproof Snuff Suede, a pigskin lining and a Vibram lug sole.
Canada's crown jewel of bootmaking is Viberg — but they make more than just boots nowadays. (See the photo above for proof.) The company's now in its third generation, remaining entirely family-owned from inception until now. Crafted using traditional techniques, their footwear is constructed from only the finest materials: "brass tacks from England, heavyweight insoles from Spain, Vibram outsoles, Swiss hobnails and the finest upper leathers from renowned tanneries in the USA and Italy."
Viberg’s Service Boot differs from most other trench boots due to its signature stitchdown construction. The silhouette is as sleek as it is tough and the Ridgeway soles make it a surefooted boot in times of rain and snow. This style is quintessentially Viberg — built to last with subtle flair.
Filson was founded in 1897 in Seattle as C.C. Filson's Pioneer Alaska Clothing and Blanket Manufacturers, an outfitter for those on their way toward claiming their stake of the Alaskan gold rush. The tradition carried through the '80s, when Filson was acquired by a former distributor. He expanded the line using traditional manufacturing techniques and materials, rendering it reminiscent to the brand we know today. In 2012, the same holdings company that owns Shinola bought Filson.
Filson's Service Boots are a timeless staple constructed from full-grain, roughout leather blended with smooth leather for a distinctive look. Suede lines the inside while a Vibram mini-lug outsole with a stacked leather heel finish off the bottom.
Frye's outfitted everyone from U.S. army men in WWII, college kids in the '70s, and cowboys. Their long lineage and expansive line make them an easy option for anyone, whether they're new to boots or a nit-picky collector.
Frye's pre-distressed Bowery Lace Up boot blends rugged workwear influences with refined tailoring, resulting in a design that's as durable as it is dressy. Goodyear welted and leather lined, they'll get even more comfortable with frequent wear.
Fresh off its 151st anniversary, Blundstone's been representing Australian bush boot lineage for nearly two centuries (well, close enough). Nearly everyone can wear and pull off Blundstones, which explains why they remain so popular. Plus, they're plenty durable and stylish in their own unique way.
Fresh off its 153rd anniversary, Blundstone's been representing Australian bush boot lineage for nearly two centuries (well, close enough). Nearly everyone can wear and pull off Blundstones, which explains why they remain so popular. Plus, they're plenty durable and stylish in their own unique way, and they’re popping up on the feet of on-trend tastemakers everywhere these days.
At one point, Vasque and Red Wing were one. They separated in 1997, but both clearly influence the other to this day. Red Wing's most popular styles date back to the 1950s, when the Moc toe took the boot scene by storm. All of the brand's heritage styles are made in the US still, including Style 875 (aka the Classic Moc).
The Classic Moc (aka Style 875) was introduced in 1952. It was a success at first, and remains so today, too. They're durable enough for a dirty job and traditional enough for everyday wear — whether with selvedge denim or twill chinos.
Red Wing also makes a Gore-Tex version for rainy days.
Grenson has been around since 1866. However, their meteoric rise is rather recent. Tim Little bought the company in 2010 and expanded its distribution to stores like Harrods and Selfridges, kickstarting serious growth. Grenson moved into New York in 2015 and celebrated its 150th anniversary the year after. They sell lots now, but the boots remain their bread and butter.
Fit for bumpy roads and city blocks, Grenson's Brady Boot sits above the ankle and has eyelets the length of its tongue. They're an excellent example of the brand's balancing of their heritage base and modern ambitions.
Tecovas was born with a singular mission: to make high-quality cowboy boots at an affordable price. Over 200 steps comprise each boot's construction, which is done by a team of artisans in Léon, Mexico. There, high-quality leather meets genuine craftsmanship, resulting in boots with hand-done cording, stitching and assembling.
You can learn all about Tecovas in our dedicated brand breakdown, which recaps its history spotlights its most popular styles.
The Dean is a sensible cowboy boot even for city folks. It has a slim shaft that can slip under tighter pants and a side-zip for easy on-off.
Rancourt had a father-son ownership structure in place from 1970 until the mid-1990s, when it traded hands. The son, Michael Rancourt, stayed on board. By 2008, the new owners decided it'd be best for the business to cease operations. Michael and his son, Kyle, reclaimed Rancourt in 2009. The brand's been on the uptick ever since, stocking everything from moccasins to derbies to durable work boots.
Made from some of the world's finest leather — Horween Shell Cordovan — Rancourt & Co.'s Porter Boots are built to last and look buttery, albeit a bit shiny. That'll fade, if you let it, but proper care can keep these clean for a long time.
Common Projects became increasingly commonplace with the rise of menswear blogs. Sites ogled at the brand's sneakers, which were simple and utilitarian yet unique. Every pair came — and still come — with a one-of-a-kind sequence on the side representing the style, color, and size of the shoe. CP's boots exploded when celebs like Kanye West rocked them. They've been staples ever since.
An instant classic since it was introduced into the lineup of luxury footwear brand Common Projects, this Chelsea boot features supple suede and a comfortable crepe rubber sole. Kanye’s been known to rock this version, but it’s not limited to hip-hop royalty.
Charles Danner, the brand's founder, forged west in the early 20th century to supply loggers with the best possible footwear for their job. The mission resulted in the brand we know today, a manufacturer rich with heritage yet eager to innovate.
A custom colorway called Smores, this version of Danner's sturdy hiking boot, the Mountain Pass, which is made in the USA from a water resistant full-grain leather upper, a Vibram outsole, Gore-Tex liners and a removable PU footbed. This is by far Danner's best boot.
Wah, wah, wah, it’s just J.Crew. I can hear every one of you boot aficionados whining now. The big mall brand may not be a shining example of generational craftsmanship, but its boots are affordable, accessible, and an incredible value considering the cost. They task factories in shoemaking regions with replicating icon styles: Chukkas, hikers, Chelseas, you name it. Give ‘em a chance. Even if just when you’re in a pinch or abiding by a stricter spending limit.
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