Heritage-style boots mix classic looks with modern materials, creating long-lasting footwear that’s sharp and solid.
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Best Heritage-Style Boots That Will Never Go Out of Style

The trend to turn away from mass-produced junk and the unsustainable eco-disaster that is fast fashion often means looking back at practices and brands that were made in the U.S. in days past. Clothing and shoes used to take time to make, with craftsman using quality materials to create long-lasting items like denim, belts, and heritage boots, burly shit-kickers designed for hardworking folks who worked in logging, oil-rigging, and on the railroads. Nowadays, these heritage-style boots are having a resurgence.

The classic, rugged good looks of these boots are being mixed with modern materials, creating long-lasting footwear that’s sharp and dependable. And the boot brands aren’t just relying on the old standard style and cut (think Red Wing Iron Ranger), they’re making more modern silhouettes that blend old with new to bring handsome, functional heritage-style boots back to life.

Best Heritage-Style Boots That Will Never Go Out of Style

Danner's Pine Grove Chukka boots are comfy but have a classic profile.
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1. Danner Pine Grove Chukka Boots

Danner has long been the go-to brand for heritage-style, USA-made boots that can be resoled after years of use. The newest line, the Evergreen Collection, doubles down on that promise with the Pine Grove Chukka. These casual boots are completely “recraftable” from the outsole and midsole to the lace hardware and stitching. Plus, the soft leather upper is mated to an oil-and-slip-resistant wedge outsole for all-day comfort.

[$220; danner.com]

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This Wolverine 1000 Mile boot has wood from Old Rip Van Winkle whiskey barrels in the heel.
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2. Wolverine 1000 Mile x Old Rip Van Winkle Boots

Fans of Old Rip Van Winkle’s legendary and super-scarce Pappy Van Winkle whiskey can pay homage to the lusted-after bourbon by picking up a pair of Wolverine 1000 Mile x Old Rip Van Winkle boots. Not only do they boast classic style and sophisticated looks, but the heel stacks are made by layering pieces of oak barrels used to age Pappy’s whiskey. The Horween leather upper is dyed a deep gray and the tongue is uniquely numbered.

[$415; wolverine.com]

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Just slip on the Chippewa Edge Walker boots for sturdy comfort.
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3. Chippewa Edge Walker Wedge Pull-On Boots

For great-looking boots that are stupidly comfortable and easy to put on, see Chippewa’s Edge Walkers. They’re plush with an open-cell foam footbed and Vibram wedge outsole, but they also have a waterproof leather upper and come with an inner liner made from a performance fabric that wicks away moisture to keep your feet dry, no matter the toil or task.

[$200; chippewaboots.com]

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The tough Red Wing Roughnecks were inspired by oil rig workers.
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4. Red Wing Roughneck Boots

Designed to withstand the rigors of manhandling dangerous oil rigs, these brutish shoes have a moc-toe upper and waxed, full-grain leather upper mated to a heavily lugged Vibram outsole with triple-stitch construction. Other premium details on the made-in-the-USA boots include nickel eyelets and a sturdy steel shank.

[$300; redwingshoes.com]

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Thursday's Logger boots are strong and sturdy like lumberjacks.
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5. Thursday Boot Co.’s Logger Boots

You can’t get much tougher or classic than footwear inspired by the tall, stout boots worn by lumberjacks in the mid-19th century, which is exactly why Thursday Boot Co.’s Logger is featured here. Not only do these waxed Horween leather kickers have a rugged lineage, they also have a unique Cuban-style heel of stacked leather that has a subtle curve in the back. Style and substance meld into one handsome, functional boot.

[$285; thursdayboots.com]

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