8 Rugged Boots To Take You Into Fall

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It’s hard to believe that we’re already in the middle August. It feels as though summer’s just begun, but fall is just right around the corner. And with the impending change of seasons comes cooler weather, so it’s time to put away those canvas sneakers and flip-flops for something that will take you through those early brisk autumn days. These boots aren’t meant to be babied; they’re meant to be worn and worn hard. Below, we’ve rounded up 8 different styles perfect for the impending cool down.

L.L. Bean 8″ Boots


Bean boots (aka duck boots) are an American classic, and it’s not hard to see why they gain new fans with each passing generation. They’re virtually impenetrable–courtesy of the hardwearing rubber base and thick leather uppers–so they’ll take you through fall and right into winter. The fact that the design has remained largely unchanged since 1911 is a testament to their quality and unrivaled utility, and they’re still made right here in the States in L.L. Bean’s factory in Brunswick, Maine.

Bean boots come in a number of different setups, with options ranging from the height of the shaft to the color of the leather. Their most versatile configuration is the classic 8″ boot in tan. They’re unlined, tall enough for even the heaviest of storms, and yet they’re comfortable enough for dry autumn days. Whether you’re trudging through the city or raking your yard, they’re a no-brainer.

J. Crew Classic MacAlister Boots in Oiled Brown Leather


Desert boots can be traced back to the Second World War, where they were first worn on the feet of British officers. Nathan Clark, great-grandson of Clark’s founder James Clark, was an officer in the Royal Army Service Corps at the time, and he liked the design so much that he brought it back with him after the War. In 10 short years, Clark’s released the desert boot, and since that time the company has been producing the venerable classic in a number of different styles, featuring a wide variety of suede and leather uppers paired with a traditional crepe sole.

Though Clark’s may be the original producer, J. Crew’s Italian-made MacAlister boots are a great take on the design. They offer a slimmer silhouette with a fully leather-lined interior and high-end uppers. They’re stitched down, not welted, so they’re probably not ideal for downpours. That said, they’re also incredibly lightweight and comfortable, and the oiled leather option will fare well against light rain and it’s sure to pick up a beautiful patina over time. And with J. Crew always running promotions, they can often be had for well below MSRP.

Chippewa Chocolate Apache 6″ boots


Chippewa is a brand known for their affordable American-made, Goodyear-welted work boots, with many models coming in at well under $200. One of their best bang-for-your-buck deals is the 6″ Apache boot in chocolate leather with a Vibram sole. These rugged boots are built to withstand the elements, with the thick rubber sole and oil-packed hide making them perfect for any inclement weather fall may bring (check out our guide for winterizing your boots, featuring the Apache 6″ boots). And should that heavy-duty sole wear out, a resole should be no problem. They might not be office-appropriate in more conservative workplaces, but they’ll make for excellent weekend beaters.

Epaulet Calgary Boots in Cognac Bison


Epaulet is a haberdashery out of Brooklyn, New York, known for their great collaborations with companies like Alden and Gitman Brothers Vintage, as well as their impeccably made and styled in-house line. Their Calgary Boots in Cognac Bison are exemplary of the latter, bringing together a beautiful last, high-end construction, and unique leather–American Bison Hide–to create a wonderful pair of boots.

Other than its unique look, American Bison Hide leather is exceptionally tough, compressed to yield the density of horsehide with a twisted grain that allows for a comfortable break in. These boots are sure to age beautifully over time, and require little to no maintenance–a little bit of brushing and light conditioning will go a long way.

Quoddy Grizzly Boots in Natural Chromexcel


Quoddy is a worn&wound favorite. Though the Maine shoemaker is known first and foremost for their beautiful hand-sewn moccasins, in the past few years they’ve expanded their catalogue with a wide range of handcrafted boots and shoes. The Grizzly Boot is one of the coolest in the collection, featuring a 6″ shaft, a gusseted deerskin tongue, and a hardwearing Vibram sole designed and made exclusively for Quoddy. The boots are lightweight and incredibly versatile, allowing for easy wear all throughout fall.

Our favorite setup is Natural Chromexcel with a red brick sole, a combination that only gets better with age. Plus, you can pair them with one of our Model 2 straps in matching Natural Chromexcel.

Allen Edmonds Long Branch Wingtip Boots


Allen Edmonds is one of the last great American shoemakers focused on classically styled footwear. Based on their incredibly popular Dalton boot, the Long Branch is a foul-weather upgrade featuring a split-reverse welt and Vibram rubber lug sole. Despite this, they’re incredibly versatile and can be worn in everything but the dressiest of occasions. They’ll look great paired with wool trousers at the office, or with a pair of jeans while you’re out walking the dog. Golden Brown Chromexcel and Black Grain Leather are both great options for the fall. And with Allen Edmond’s recraft program, they’re sure to last a lifetime.

Oakstreet Bootmakers Brown Trench Boots


Chicago-based Oakstreet Bootmakers began by producing hand-sewn moccasins, but the company has since expanded to include a number of different styles of footwear, among them boots, derbies, and chukkas. The Trench Boots are the anchor of this collection, based on a style worn by soldiers in World War I. The modern take is decidedly stunning, featuring Horween uppers, a fully lined interior, a stacked leather midsole and Dainite outsole, and Goodyear construction for long-term wear and tear.

Alden Indy 403 in Horween Chromexcel


Alden is beloved for their classic American styling, high quality Goodyear construction, and wide range of accommodating lasts. One of their most iconic styles is the Indy boot, named after the legendary film character played by Harrison Ford. The story goes that Ford wore his personal pair of Indy boots (then simply called by their reference number, 405) throughout production, refusing to wear the boots given to him by the wardrobe department because they were too uncomfortable.

The 403 Indy boot takes everything that was great about the 405 and tops it off with Chromexcel uppers from Chicago’s Horween tannery. It’s a beautiful shade of brown with strong red undertones that make for a surprisingly versatile pair of boots. Pair them with jeans or slacks for a smart look.

Ilya is Worn & Wound's Managing Editor and Video Producer. He believes that when it comes to watches, quality, simplicity and functionality are king. This may very well explain his love for German and military-inspired watches. In addition to watches, Ilya brings an encyclopedic knowledge of leather, denim and all things related to menswear.
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