Unless you’re on the brink of a Margaritaville beach retirement—drink in hand, toes in the sand (wow, that does sound nice)—now’s the time to start prepping your cold weather wardrobe. Even those committed to toasting in the tropics year-round can’t deny the coziness of chillier climes. Crisp air and kaleidoscope foliage. Hot toddies by a crackling fireplace. Oh, and a steady rotation of kick-ass men’s boots to show winter who’s boss.
There are boots out there for every occasion. Hiking boots that can take you from the trail to the tailgate. Desert chukkas and badass work boots for the office (if you ever end up going back). Chelseas and jodhpurs for when you want to class it up at a warehouse art show or fancy eatery. The list goes on.
That said, there’s limited cash in your bank account and limited room on your shoe rack. (Ankle-high footwear takes up a ton of space; we get that.) When shopping for men’s boots, don’t focus on quantity. Instead, be strategic and invest in boots that’ll pay style dividends in the future. That means stocking up on pairs that are sturdy enough to outlast several winter seasons and timeless enough to outlive fleeting trends. Below, we’ve highlighted 11 boots across a range of styles that we’re adding to our post-September shoe portfolio.
The Best Men’s Boots
1. Clark’s Desert Boot
Did you know Clark’s most iconic boot actually has its roots in the desert? Founder Nathan Clark modeled his unfussy chukkas after a rough boot he spotted while strolling through Cario’s Old Bazaar way back in 1950. The minimalist design remains pretty much identical to the very first pair, though dozens of versions have been spawned in the following decades, including this leather-free suede style with a signature (and sustainable) crepe sole.
Paul Stuart’s Mansfield Beetle Boot is super sleek, made in Italy, and comes with a sporty rubber sole in contrasting black and white. You’ll definitely turn heads ambling down the sidewalk in these souped-up Chelseas, but they’re also versatile enough to pair with anything from jeans to pleated wool trousers.
Few brands have tackled the function-meets-fashion evolution of the hiking boot like Danner. With its retro laces and Saved by the Bell colorways, the Free Spirit looks like a relic from the late ‘80s, but these boots are upgraded with modern tech like a suede and abrasion-resistant nylon upper that’s breathable and waterproof (thanks to a Gore-Tex liner). The dual-density midsole is firmer around the edges for enhanced stability, and a Vibram outsole offers plenty of grip on slick streets.
The Roughneck is one of Red Wing’s oldest shoe styles. It’s an offshoot of a boot originally worn by oil rig workers, whose notoriously perilous work earned them the nickname “roughnecks.” Your cushy desk job might not lend you much street cred, but this hard-wearing six-inch moc with a triple-stitched, Goodyear welt construction surely will.
Moncler, the French emperor of winter jet-set style, released the perfect shoe to cap off the après-ski look—and thankfully, it isn’t a snow boot. The oatmeal nubuck Mon Corp is an uber-fashionable ankle boot set on a glacier of a lugged sole. It comes complete with tricolor rope laces and a padded leather topline emblazoned with the Moncler logo.
Who says “safe” is a bad thing? Polo Ralph Lauren’s Bryson Suede Chelsea is an affordable low-key classic that can do no wrong, as far as we’re concerned. The timeless, benchmade boot has oiled suede uppers with elasticated sides and a heel pull tab—making it a cinch to pull on and off—plus a cushioned footbed for all-day comfort.
7. G.H. Bass & Co. Camp Moc III Ranger Full-Grain Leather Boots
The Maine brand that invented the penny loafer also makes a damn good boot for any guy’s fall and winter wardrobe. Bass’s Camp Moc III Ranger is both smart-looking and solidly built with tumbled full-grain leather, classic moccasin stitching, antique eyelets woven with leather laces, and a comfy EVA sole.
This classic utilitarian boot features all the signature aesthetic pops you’d expect from Dr. Martens—yellow-scripted pull loop and welt stitching, chunky air-cushioned sole, grooved sole edges—but it’s also 100-percent vegan. It’s made from a soft and supple synthetic leather called Felix Rub-Off.
Camper’s lightweight Ground boot is crafted with suede sourced from a Gold Standard tannery certified by Leather Working Group, an NGO that assesses the environmental compliance of leather manufacturers. Fusing an industrial aesthetic with urban street style, the Spanish shoemaker partnered with Michelin to produce the chunky rubber outsoles on these boots: They use the same open tread pattern as Michelin e-bike tires for exceptional grip on any surface.
Diemme draws on the rich shoemaking heritage of Italy’s Veneto region with its Verona boots. They’re made from premium all-Italian materials including a calf-leather lining and an extended lug sole with a decorative welt and tonal stitching.
Marked by a low heel and buckled strap that fastens around the ankle, the jodhpur is an equestrian-inspired boot created as an alternative to knee-high riding boots. To Boot New York’s style-forward Clarence version is made of Italian calf suede jazzed up with a polished silver zip and side buckle.