Summer is officially over. Once September rolls around, you start to think about trading in your flip-flops for some proper footwear. Footwear that will keep your feet warm and dry through rain and sleet and snow. The kind that requires socks. Boots.

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Because boots have been such a mainstay of the male wardrobe for centuries, it’s easy to find a pair, but it’s not always easy to find a high-quality pair. A pair that’s worthy of your hard-earned money. A pair that’s worthy of the time you’ll spend breaking them in until they fit just right and have just the right amount of scuff marks to prove that you’ve lived an exciting life. Never fear—we’ve rounded up 21 of the best boots to tromp around in this fall, whether you’re hiking with your buddies, heading to work on casual Friday, or getting dragged to another apple orchard by your girlfriend. Girlfriends love apple orchards.


Palladium Pallabrouse Boots

Palladium got its start in 1920s France, making vulcanized rubber tires for airplanes. In the late 1940s, they made the switch to creating footwear with rubber soles as hard charging as their tires, and since then, they’ve built a brand committed to creating quality shoes that will stand the test of time. Made from a combination of cotton and canvas twill as well as a molded rubber sole, the Pallabrouse Boot is the perfect addition to your Fall wardrobe.

Purchase: $80


Native Fitzsimmons Jiffy Boots

Some of Native’s offerings feel a bit out of this world, and its Fitzsimmons Jiffy Boots are no exception. Available in a variety of colors and patterns and made with lightweight EVA (and lined with breathable neoprene) and a bouncy sole, you’ll be able to take a giant leap (or two) of your own in these, for sure.

Purchase: $90


Clarks Desert Boots

In 1949, while stationed in Burma, Officer Nathan Clark noticed the desert boots other military members were wearing to keep themselves comfortable in the harsh desert conditions. Back in his native UK, Clark created his own version of the Desert Boot, which is still sold today, even 60+ years later.

Purchase: $130


Cole Haan Lennox Hill Chelsea Boots

Chelsea Boots have been around since the Victorian Era but it was the mod scene in 1960s England that really popularized the style (and guaranteed that the name “Chelsea” would be permanently attached to it). The point? These classic no-frills boots (available in brown and in black) will never go out of style, and will look just as good with a suit as it will with a pair of black skinny jeans.

Purchase: $132


Oliberte Gando Pullup Boots

Started in Ethiopia in 2009, Oliberte is the first fair trade certified footwear company, but just because they’re charitable doesn’t mean they’re not fashionable. These Gando Pullup Boots are as gorgeous as they are well made, featuring a reddish leather exterior with a 100% goat leather lining and a jagged rubber sole to ensure sure footing.

Purchase: $160


Original Chippewa Service Boots

A true American heritage brand, Chippewa (named for its home in Chippewa Falls, Wisconsin) has been creating quality footwear since 1901. Crafted out of full-grain leather, featuring a high-quality Vibram sole, leather laces, and a guarantee that they need zero time to break-in, they’ll quickly become your new favorite boots.

Purchase: $220


Sperry Gold Cup Bellingham Cap Toe Boots

Sperry is known for being the king of boat shoes, but surprise—you can wear Sperrys all year ‘round with the introduction of the brand’s boot line. The Gold Cup Bellingham Boots sport a classic silhouette, but they incorporate key features that you’d only find in a nautical-based brand. The boot features a genuine lambskin lining for extra comfort and the rubber soles feature Sperry’s patented molding to provide increased traction on both wet and dry surfaces.

Purchase: $225


Woolrich Footwear Yankee Horween Boots

“They don’t make things like they used to,” your grandfather used to complain, and while grandpa might be right about that for some things, but not about Woolrich. They’ve been around since 1830, and they’re still producing quality made-in-the-USA products, like these Yankee Horween Boots. Made from quality Horween leather and utilizing Vibram soles, they’re handsome enough to be worn from the field to the French restaurant.

Purchase: $250


Grenson Jacob Chelsea Boots

UK-based Grenson has been creating quality footwear since the 19th century, and these Chelsea Boots are no exception. Made from high-quality leather (and featuring Grenson’s signature punched brogue detailing), they feature elasticated side panels and a canvas heel pull, which will make it easy to kick ‘em off and put ‘em on. Who has time to spend with laces anyway?

Purchase: $273


Broken Homme Davis Oxblood Boots

California-based Broken Homme is more than just a company with a clever name. Everything they make is fully crafted in the USA, and its handsome line of boots are made to go from an afternoon dirt biking with the guys to an evening in the city with your fiancé. The Davis boots will do exactly that, with its rich oxblood coloring, sturdy Vibram heel, and sleek black leather laces.

Purchase: $289


Kendal & Hyde Co. Goodyear-Welted Boots

Relatively new leather goods company Kendal & Hyde Co. follows the TOMS model, where they give away a pair of shoes to a person in need for every pair of shoes they sell. You can feel good about supporting that ethos while simultaneously feeling like you made a solid investment—these boots are made to last. Crafted from full-grain leather (you can choose from a variety of colors), the boots are Goodyear-welted, which means they’ll stay together longer than shoes that are glued together.

Purchase: $299


Red Wing Harvester Boots

Red Wing—named after its home in Red Wing, Minnesota—has been cranking out quality footwear since 1905, so you can wear the heritage boots that legions of admirable men in your life have worn for decades. This version of the Harvester Boots marks the reintroduction of one of Red Wing’s most popular offerings—with its Amber Harness leather, antique brass hardware, and Vibram sole, these are

Purchase: $320


Danner Mountain Light Timber Boots

Out of the Depression era came Danner boots, which was established in Oregon in 1932 by Charles Danner, a man who believed that craftsmanship and quality mattered regardless of the economic climate. That belief in quality still drives the company 80 years later. The Mountain Light Timber Boot is an updated version of the popular Mountain Light, which was originally produced in 1979. Crafted from full-grain leather, the boot is lined with breathable Gore-Tex material, and features a Vibram Gumlite sole, meaning the shoe is incredibly durable while still being comfortable.

Purchase: $360


Thorogood Dodgeville Boots

Founded in 1892 in Wisconsin, Thorogood still uses the techniques that it perfected during its 100+ years of making boots. The Dodgeville boot is one of Thorogood’s most popular offerings, with a classic silhouette and cap toe design crafted out of Horween Chromexcel leather.

Purchase: $375


Rancourt & Co. Moto Boots

Maine-based Rancourt & Co. has been crafting leather goods since the 1960s, and the Moto Boot is one of its best offerings. Crafted from full-grain steerhide, these classic boots feature a double-layered cap toe, waxed nylon laces, sturdy Vibram sole, and antique brass eyelets.

Purchase: $398


Quoddy Grizzly Boots

At Quoddy—a shoemaker named for the small town of Passamaquoddy, Maine where it was founded—they take the term “handmade” very seriously. Every shoe is so made-to-order that you can choose the coloring for everything on your pair of boots—the upper leather, the sole, the thread, the hardware, and even the lining.

Purchase: $400


Oak Street Bootmakers Black Dainite Trench Boots

Chicago-based Oak Street Bootmakers has been crafting quality boots for over 20 years, just like these Black Dainite Trench Boots. Crafted out of black Horween Chromexcel leather, these boots are truly tough as nails, and made to last just as long.

Purchase: $462


Filson Waterproof Uplander Boots

For over 100 years, Filson has been crafting quality apparel and gear that will help you trudge through the forest as easily as you trudge down the block on your way to the office, and these Uplander Boots are no exception. Made from full-grain leather, the boots feature a removable cork insole that will mold to your foot to ensure comfortability, a quick-drying liner to keep you and your socks dry (Lt. Dan says it’s the most important thing), and a Vibram sole to keep you from slipping.

Purchase: $475


WANT Les Essentials de la Vie Montoro High Boots

Montreal-based WANT Les Essentials de la Vie is specializes in travel goods, but what’s a more important travel accessory than what you wear on your feet all day? The Montoro High Derby will look like a classic derby shoe when worn underneath your suit, but the high ankle will keep you warm and dry during the winter months. Crafted out of high-quality calfskin leather, the boots are available in black, brown, burgundy, and navy.

Purchase: $575


Viberg Service Boots

Started in the 1930s by a guy named Ed, Viberg has been creating quality footwear for over 80 years. The Service Boot is an updated version of the original Viberg boot, designed by Ed in the 1930s, which sports the classic silhouette of boots worn by enlisted men during WWII.

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Purchase: $690


Common Projects Mechanic’s Boots

Common Projects wares’ are anything but common, which is why they’ll typically cost you a mint. You might think it’s insane to shell out nearly a grand for a pair of work boots, but while Common Projects’ Mechanic’s Boot might look typical, it’s anything but. Crafted out of premium leather in Italy, these boots feature a unique moc-toe and a sturdy, comfortable crepe sole, which will quickly make them your favorite pair of boots in your closet.