The Best Boots for Men: Every Style and Silhouette Worth Stocking In Your Closet

The best boots for men have serious range. The right pair of boots can traverse the social complexities of a holiday work party as ably as the treacherous terrain of a jagged mountainside. Okay, so you’re probably not kicking up your feet at the beach with some honkin’ leather boots. But barring tropical endeavors and, like, sports, there aren’t many situations where boots can’t hang. So, yes, there’s a boot for practically every situation—but only a select few will get you through each of them without looking like a damned fool. Whether you’re in need of some hard-wearing boots for sweat-inducing labor, a pair of posh and polished extendo-brogues for your next black tie affair, or just some rodeo-ready cowboy boots to stunt on the city folk, these are the best boots for men around.

Trekking through tough terrain? Making good on a forgotten promise to enjoy the outdoors with your friends? You’ll need an actual pair of hikers to help you survive Mother Nature’s playground—boots with great cushioning, heavy-duty water-resistance, plenty of breathability, and, naturally, grippy rubber outsoles. Of course, the raddest hiking boots can also take easily to the concrete jungle, where the most grueling demands they’ll be subjected to are that of your own drip.

Season Three “The Ansel” boot

Danner Mountain Light 2 hiking boot

Introduced back in the ‘70s, Danner’s signature boot was a revelation for the hiking scene, merging tough leather and even tougher construction with a futuristic Gore-Tex waterproof membrane.

Merrell Moab 2 mid hiking boot

Salomon X Ultra 3 mid GTX hiking boot

Chelsea boots are sleek, smooth, and easy to get into. The pull-on style’s got no laces to trip you up, which gives them a streamlined silhouette that, when paired with the right leather, is perfect for dressier affairs. But they can get down and dirty too, and often look all the better for it. (Their rocker pedigree also makes them a great option should you find yourself performing in front of thousands at MSG).

Blundstone Chelsea boots

Still the best all-weather boots on the planet—now updated with eye-grabbing hits of fire engine red.

Jack Erwin “Ellis” rubber sole Chelsea boots

R.M. Williams “Gardener” whole-cut leather Chelsea boots

Saint Laurent “Wyatt” Chelsea boots

Spending long hours on your feet with a bunch of tools strapped to your belt? (Or just want to play up the workwear energy in your daily fits?) A pair of high-quality work boots is what you need. Ideally, you’ll want something with supreme cushioning, comfy and grippy rubber soles (look for that Vibram stamp), and maybe even a steel toe or two. Either way, your wardrobe will benefit from the extra style points a pair of these bad boys will add.

White’s Boots 350 Cruiser MV boot

Thorogood American Heritage 6″ moc toe boot

All-American boots at an All-American price.

Timberland 6″ premium waterproof boot

Nearly 50 years into their run, it’s hard to top Timberland’s original lug-soled, nubuck leather, wholly waterproof work boots.

Red Wing Heritage classic moc boot

Desert Boots and Chukka Boots

If you’re looking for a decent sneaker approximate with plenty of rugged appeal, desert boots offer maximum comfort without compromising on their essential boot-iness. With their telltale crepe soles and suede uppers, they’re some of the chillest boots on the market, ready to kick it with some shredded jeans and a vintage tee just as willingly as a suit and tie.

Drake’s “Crosby” moc-toe chukka boot

Dress Boots

Not all boots are designed to help you scale cliffs or slog through the mud. Sometimes, duty calls for a boot that can charm its way through high society and hop from a luncheon during the day to a gala at night. Stay away from the chunky lug-soled shit-kickers and opt for something with luxurious, smooth leather uppers that can shine up to a mirror finish.

Allen Edmonds “Dalton” boots

Our Legacy Camion square-toe leather boots

Kingsman x George Cleverley cap-toe pebble-grain leather boots

Tricker’s x Todd Snyder Stow boots

Cowboy Boots

Hear us out: Cowboy boots might be the most stylish of them all. They come in a grip of silhouettes, often accented by intricate stitching, lofty heels, and sharp toes. And sure, you may not be making your way to the local honky-tonk bar, let alone riding a horse on a daily basis, but you definitely need to get dressed. The most surefooted way to get your style point average up is with some rodeo-ready shoes.

Tecovas “Cartwright” western boots

Dan Post Boots Milwaukee round toe boots

Eytys “Luciano” leather western boots

Rhodes Footwear roper boots

Combat Boots

Somewhere between work boots and dress boots are combat boots. They’re usually unadorned black leather lace-ups set atop chunky rubber lug soles, and they appeal to everyone—from the heady avant-gardists, to the vintage-loving thrifters, to the sworn Dr. Martens devotees. In other words, if you carry yourself with any sort of vibe, combat boots can match it.

Dr. Martens 1460 service boots

Julius leather combat boots

Belstaff storm leather and webbing-trimmed Cordura boots

Rick Owens Beatle Bozo tractor boots

Rain Boots

When the forecast is predicting showers, an umbrella and a raincoat, no matter how good, will only get you so far. (Need we remind you how absolutely grody wet socks feel?) Don’t risk stepping out in sneakers—or boots!—that aren’t built for inclement weather. Get yourself some waterproof rain boots or slush-defying, insulated winter boots, and glide through slippery weather with swag.

Totes Cirrus ankle rubber rain boot

Muck Boot Company muck chore boot

If you need your rain boots to also be mud boots, these can take on the gunk with ease. The beefy outsole tread pushes through mud easily while the thick layered toe provides protection. 

Hunter original tall rain boot

When it comes to rain boots, Hunter should be the first to come to mind.

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