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.
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.
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. 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. 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. In 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.
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.
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.
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.
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.
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.
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.
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.
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.)
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. But they’re not 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.
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."
These are super-specific recommendations, but that's because Carroll's done plenty of testing up to this point. Celebrity men's stylist, Vanessa Powell, on the other hand, 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.
