10 Best Men’s Boots for Fall 2019

From rugged chukkas to hardwearing hikers—Huckberry’s own Head of Footwear offers up some of the best men’s boots for our favorite transitional season
November 1, 2018Words by Huckberry Staff

Head of Footwear Charley Allen
Huckberry Head of Footwear Charley Allen

Hey, Charley here, Huckberry’s Head Footwear Buyer. Listen, I might be a little biased, but fall is by far my favorite time of year—not just because I’m from the northeast and have a weird soft spot for the leaf-peeping months—but because it’s finally boot season. After a summer spent wearing lightweight slip-ons and sandals, it’s finally time to reach for those substantial, hardwearing boots

In honor of this transitional time, I’ve rounded up my favorite go-tos for this side of the autumnal equinox. We’re talking everything from reliable, weather-proof work boots to handsome everyday chukkas.

And we get it. New boots are a huge investment both money-wise and time-wise (considering how long they’ll last), and every boot out there was purpose-built for something different. So in order to make sure you end up with the right pair: read on, take our quiz, consider the benefits of every style, and happy boot season.
 

 


Rhodes Dean Boot
 

The Rhodes Dean Boot


Great for: 

The office, going out for drinks, suiting up, making a good first impression  

About the boot:

Even today, the Old World is still looked on with reverence when it comes to the best men’s dress boots. That’s why we crossed the pond to partner with the legendary Rhodes Footwear to bring its Dean Boot to the US. This Huckberry exclusive is crafted from calf leather in the company’s Portuguese factory where shoes have been constructed in the old ways for the past 50 years. Breathable, odor-resistant, and long-living, these are boots that elevate every outfit. We also love the three rows of speed hook lacing, which allow you to whip these on in the morning and get out the door. The best part: When its sole finally gives up the ghost, bring them to your local cobbler, who can easily re-shod these comfortable dress boots for a new lease on life. 


SHOP THE DEAN BOOT
SHOP ALL RHODES FOOTWEAR

 


 

Rhodes Dylan Chukka


Rhodes Dylan Chukka
 

Great for:

Everyday wear, dropping by your favorite beer garden, heading into the office

About the boot:

Desert boots were originally designed to withstand the harshest arid climates in the world, which makes them a sharp-but-casual boot that keeps on giving, mile after mile, no matter what you put ‘em through this season. When you take the rugged desert boot design and put it together with Rhodes’ signature craftsmanship and only the highest-quality materials, you get the Dylan Chukka, an essential everyday boot with enough versatility (and comfort) for almost any event penciled into your September-December calendar.


SHOP THE DYLAN CHUKKA
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Astorflex Greenflex - Exclusive
 

Astorflex Greenflex - Exclusive

Great for:

Not spending your life savings on a quality pair of boots (so you can spend it all at Oktoberfest instead)

About the boot:

Handmade in Northern Italy by a family that's been making boots for six generations, these boots are eco-friendly, handsome as hell, and represent the best value on the market. When we teamed up with them to build these exclusive Greenflex Chukka Boots, we chose this special nubuck leather—with a slightly waxy finish, it’s super soft and supple, and will wear in beautifully over time. The boot is then finished with 100% natural rubber soles that make any on-your-feet job a hell of a lot comfier—whether you’re bagging leaves in the front lawn or heading into your 9-5.


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The Best Chelsea Boot: Rhodes Chelsea


Rhodes Huxley Boot
 

Great for: 

Everyday wear, nights out for drinks, dressing up with a suit

About the boot: 

If you’ve been paying attention to Huckberry over the past year or so, you’ll see that we’re obsessed with Rhodes boots. Their classically styled Dean boot had us clamoring for more, so they obliged and stepped in to make the more avant-garde Chelsea boot. As third-generation bootmakers, quality was never in question, but with this new release, we know that style is undisputably equal in importance at Rhodes.


SHOP THE RHODES HUXLEY BOOT
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Danner Vertigo 917

Danner Vertigo 917

Great for: 

A full day on your feet exploring your own city, playing tourist in a new one

About the boot:

Drawing on their decades of experience designing the best hiking boots around, Danner designed the Vertigo 917 with the urban explorer in mind. Outfitted with a handsome, full-grain leather upper with superior waterproof protection—these boots come with a supremely comfortable ride, lightweight sole, and twin gores for easy on and off. All of which makes them more than ideal for any urban adventure you find yourself on this fall. 


SHOP THE DANNER VERTIGO 917
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Quoddy Bowhunter Boot


Quoddy Bowhunter Boot


Great for:

Getting made-to-order quality without the wait

About the boot: 

The Quoddy workshop produces their signature handsewn moc-toe boots and shoes at unrivaled levels of handmade quality. Based in Lewiston, Maine, most of their business is made-to-order footwear, but we managed to snag a few pairs of ready-to-wears in our favorite styles. The Bowhunter Boot is a classic moc toe boot, with a bellows-style tongue that’s built to keep your feet dry during heavy use in the field.


SHOP THE BOWHUNTER BOOT
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Rancourt Wolf Boot


Rancourt Wolf Boot 


Great for:

Everyday wear, going out for drinks, suiting up

About the Boot:

When most would be receiving a silver watch, sheet cake, and a family party, Rancourt & Co. is celebrating its 50th birthday by releasing the Huckberry exclusive Wolf Boot. Available in smooth Chromexcel cow leather from Chicago’s Horween Tannery or Tasman Tannery’s textured bison leather, these materials are then hand-worked at Rancourt’s Maine factory for in the rare Made-in-the-US tradition. Utilizing the Blake welt technique, when these men’s dress boots wear through their soles, have them resoled and keep the tradition—and the miles—rolling.  


SHOP THE WOLF BOOT
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Red Wing Iron Ranger


Red Wing Iron Ranger


Great for:

Everyday wear, chopping wood, iron mining

About the boot:

At this point, Red Wing doesn’t really need an introduction. If you’ve had your finger anywhere near the pulse of men’s boot culture, you’ll know that Iron Rangers are a staple piece in the wardrobe—for both work and play. Originally made for gold rush miners in the 1800s, these boots are built with leather from S.B. Foot Tanning and a Goodyear-welted Vibram sole—fit to take a beating and last a lifetime. Red Wing’s master craftsmen in Minnesota put so much care into the construction, the Iron Ranger is a boot you really only need to buy once. Once broken in, no pair is the same, and that lived-in feeling only gets better with time. (If you’ve yet to pull the trigger on your first pair of Red Wings, our friend Brad Spychalski’s reflection on his purchase 10 years later might just convince you.)


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Helm Hollis Boot


Helm Hollis Boot - Exclusive


Great for:

Going from the lumbar yard to an upscale cocktail bar

About the boot:

Any self-respecting Texan will tell you that a pair of boots is as important as high school football. That being said, for the Austin-based folks at Helm Boots, putting in countless hours designing innovative, supreme-quality boots, is far more important than the Friday night lights. Every inch of their classic Hollis Boot showcases the attention to detail and thoughtful construction that harks Helm Boots as a trail-blazing brand in men’s footwear. This heralded quality and handsome design never waver, and it’ll continue to be top-tier years after you first take ‘em out of the box.
 

SHOP THE HOLLIS BOOT
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Truman Service Boot - Exclusive


Truman Service Boot - Exclusive

Great for: 

Wearing every day for the rest of your life

About the boot:

Vince Romano founded Truman Boot Co. to bring American-made quality back to a world that had settled for disposability—his vision quickly gained traction, and Truman Boot Co. After heading west from Pennsylvania for open pastures a few years back, their business and each pair of their ruggedly handsome boots, like the Service Boot, is still handmade in their Oregon workshop. These stunning boots are made from premium leather hides sourced from Charles F. Stead tannery in Leeds, UK, finished with polished brass hardware, and built with a resoleable 270 Storm Goodyear welt.


SHOP THE SERVICE BOOT - EXCLUSIVE
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For more fall boots, check out Adventure Sports Network’s 2018 roundup



>>Next: The Art of Shoe Maintenance
 


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