The 20 Best Boots to Lace Up, Pull On, and Stomp Around In This Fall

Yes, sure, we all love sneakers and slippers and sandals. They’re comfy! And no one is going to blame you for reaching for the comfy stuff. But man cannot live on soft shoes alone. Fall is on its way and it’ll be bringing weird weather with it. Anticipate rain. And fog. Maybe a bout of sleet or two because the world we’re living in right now. Your sandals can’t handle that shit. Your slippers belong indoors. And while your sneakers might hold up for a bit, they aren’t really made to endure the elements in an ongoing manner—unless they are. But even despite existence of winterized, weather-beating sneaker, you still need something more. You need boots.

Why? Well, because they look the part. Even the toughest sneakers don’t telegraph the take-no-prisoners attitude a great pair of boots does. We’re back out in the world now, and people are starting to really tune in their fits. Do you honestly want to be the guy who doesn’t know how to build a look without a swoosh or a trio of stripes in the mix? Of course you don’t. You know that everyone out there is stepping his game up, which is why loafers had such a smash-hit summer. And you know what the fall equivalent of the loafer is (other than…the loafer)? Boots, baby!

So, if you’re ready to get back into the swing of things, know that there’s no better time to invest in a trusty pair of boots than right now. Not sure what to get? We got you. Below is a breakdown of five boot styles you should keep on your radar this fall—and, really, all year long—to help make sure you get your search started on the right track.

The Chukka Boot

The chukka, also commonly referred to as the desert boot, has a long and illustrious history as one of the smartest forms of casual (though not too casual) footwear around. Perhaps the most famous stylish dude to wear them on a regular basis was actor Steve McQueen—and copying McQueen when getting dressed is, unquestionably, always a solid move.


Scout Chukka Boots

Thursday Boot Company Scout Chukka Boots

Desert Boots

Clarks Desert Boots

1990 MacAlister Boots

J.Crew 1990 MacAlister Boots

Chukka Boots

Nisolo Chukka Boots

The Brogue Boot

Brogue boots: Like your beloved brogues, only taller! (And, to be honest, maybe even better.)


Livingston Boots in Plaid

Taft Livingston Boots in Plaid

Fred Leather Brogue Boots

Grenson Fred Leather Brogue Boots

Black Leather Lace-Up Boots

Toga Virilis Black Leather Lace-Up Boots

Stow Boots

Tricker’s + Todd Snyder Stow Boots

The Chelsea Boot

Four upstart lads from Liverpool transformed an otherwise under-the-radar boot style into an iconic footwear silhouette almost overnight, and the rest, as they say, is history. For good reason, too: A solid pair of Chelseas is still one of the best boot-related investments a man can make.


Sonoma Suede Chelsea Boot

New Republic Sonoma Suede Chelsea Boot

Now 23% Off

Suede Chelsea Boots

R.M.Williams Suede Chelsea Boots

Drugstore Glossed-Leather Chelsea Boots

Celine Homme Drugstore Glossed-Leather Chelsea Boots

Logo-Print Suede Chelsea Boots

Off-White Logo-Print Suede Chelsea Boots

The Lace-Up Boot

If you’re looking for a bit of edge but still feel like the Chelsea is a touch too rock ‘n’ roll, the lace-up is an ideal alternative. In black leather, it’s got a little bit of a punk-ish vibe, but the silhouette generally remains dressier than it’s actual combat boot counterpart. Which means, crucially, you can wear it with a far wider range of outfits, especially if you go for a pair in suede.


6" Boondocker Boots

Golden Fox 6″ Boondocker Boots

Now 14% Off

Caribou OTM Boots

Sorel Caribou OTM Boots

6 Inch Premium Waterproof Boots

Timberland 6 Inch Premium Waterproof Boots

Captain Cap-Toe Leather Boots

Thursday Boot Co. Captain Cap-Toe Leather Boots

The Combat Boot

Of course, if lace-ups are still too conservative for you, going all out with a classic pair of combat boots is always a play. To this day, few brands do the style better than Dr. Martens, and the nostalgia for select ’90s silhouettes taking modern menswear by storm certainly doesn’t hurt. Try a pair of the shoemaker’s classic 1460 boots if you really want to wholeheartedly embrace the punk-rock spirit that first made the style a bona fide icon. And as previously stated, they work work great in the rain, too.


1460 Combat Boots

Dr. Martens 1460 Combat Boots

Laker Combat Boots

AllSaints Laker Combat Boots

Spongesole Combat Boots

Off-White Spongesole Combat Boots

Monolith Combat Boots

Prada Monolith Combat Boots

Jonathan Evans is the style director of Esquire, covering all things fashion, grooming, accessories, and, of course, sneakers. He lives in Brooklyn with his wife and son. You can follow him at @MrJonathanEvans on Twitter and Instagram.

Barry Samaha is the former style commerce editor at Esquire, where he covered all things fashion and grooming. Previously, he was an editor at Harper’s Bazaar, Surface, and WWD, along with overseeing editorial content at Tod’s Group. He has also written for The Daily Beast, Coveteur, Departures, Paper, Bustle Group, Forbes, and many more. He is based in New York City and can’t seem to find enough closet space for all his shoes. 

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