The Best Leather Boots to Wear This Fall

Autumn: It seems like every year this season pops up out of nowhere, tightening its pumpkin spice-flavored grip across the northern hemisphere. But no matter how you slice it, you’re gonna have to gear up those feet with some reliable footwear. And what better way to defend your dogs than leather boots. For the guys who won’t allow rain, snow, sleet, and everything in between stop them in their tracks (or you just want some stylish boots to wear), here are a few of the best leather boots for men to buy this fall.



From chukkas to hard-working and sturdy boots you can take on a hike, these will be able to last you through the wintertime in style. And once you find the right fit for you, don’t forget to wax up and weatherproof your boots.

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Red Wing Heritage Blacksmith Boots

We’ve said it before, and it won’t be the last time, either: You will want to wear your Red Wing Heritage leather boots everywhere you go, forever. Invest in a pair of its Blacksmith kicks, and you can expect these beauts to last you for years. Pro tip: We recommend going directly to a store to get your boots fitted. If you can’t make it to a physical shop, consider going down a half size so the leather can stretch and mold to your foot. 

[$ 300;]

Courtesy of Redwing

Thursday Vanguard Boots

Back in 2014, Thursday hit the ground running by offering a huge selection of boots, shoes, briefcases, and belts for the stylish, on-the-go guy. The brand puts a major value on craftsmanship—a quality you can see and feel when slipping into the Vanguard boots. A rendition of American service boots from the 1940s, the Vanguards get hand-stitched here in the States. Ths pair’s water-resistant, but the studded rubber outsoles mean you can truly slip these on no matter the conditions this season. 

[$ 265;]

Courtesy of Thursday Boots


Every guy should have their go-to. Go-to jacket, go-to watch, go-to sunglasses. Meet a top contender for your next go-to boot: the HELM Zind boots. This versatile leather pair can be worn with a suit as easily as it can be rocked with jeans while giving you excellent protection against the elements. This is the type of handcrafted boot that lasts—so make sure you take care of yours.

[$ 399;]

Courtesy of HELM

Florsheim Foundry Plain Toe Chukka Boots

If you’re looking to step out of your comfort zone just a bit this season by adding color to your wardrobe, go with a timeless style of Horween leather chukkas like this classic pair from Florsheim. The subtle green leather works with anything you throw on with them. It also comes in four other colors, from tan to burgundy, so you can find the right one to fit your style. (And if you want a behind-the-scenes peek at how the brand makes some of its coolest boots? We’ve got the inside look.)

[$ 280;]

Courtesy image

Danner Forest Heights II

Portland, Oregon-based Danner has been making some of our favorite boots for decades. And more than likely you’ve already been rocking its pairs of hiking and everyday footwear. (We wore this pair nearly all summer, from work to hiking upstate.) For something on the more formal side, try its Horween leather Forest Heights IIs that offer a bit of extra polish for days you’re wearing your suit to the office. Bonus: They’re still grippy in case you decide to take a long lunch and find a nearby trail.

[$ 290;]

Courtesy of Danner

Timberland Kendrick Waterproof Chukkas

Do-it-all leather boots under $ 200 that’s big on style but won’t hurt your feet? Enter Timeberland and these simple Kendrick Waterproof Chukka boots. They support your feet with full-grain leather uppers, a comfortable footbed, and, yes, a waterproof design that’s essential on cold, rainy fall days. You can’t beat that kind of deal.

[$ 160;]

Courtesy of Timberland

Beckett Simonon Gallagher Boots

Beckett Simonon has been on the scene for a few years now, breathing life into the made-to-order footwear scene with a fresh release of cool-as-hell shoes and boots each month. For the unpredictable months of early autumn, its Gallagher Boot is a great way to stay warm, dry, and look stylish the entire time. Made from full-grain leather, these versatile boots offer a handsome alternative for a price that won’t drain your bank account. If you’re heading to a fancy event that isn’t boot-friendly, check out its business casual Cohen Loafer

[$ 219;]

Courtesy of Beckett Simonon

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