The 8 Best Men’s Dress Boots

Upgrade this season’s outfits with our favorite footwear
September 26, 2019Words by Jon Gugala

Boots have always had their place on the ranch, in the mountains, and under your favorite jeans. But thanks to intrepid shoemakers and materials once used solely for lace-ups, some of our favorite men’s dress boots can now peep from under your suit hems during a night out. The rules are simple: add some shine to that leather, and that faithful footwear becomes a refined gent out on the town. Their look fits well with a two-piece suit, and yet, come the weekend, they’ll elevate selvage denim and an Oxford with ease. Read on for the best men’s dress boots this season.
 



Rancourt Wolf Boot


Rancourt Wolf 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 the rare made-in-the-US tradition. When these men’s dress boots wear through their soles, have them resoled and keep the tradition—and the miles—rolling.  


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Rhodes Dean Boot


Rhodes Footwear Dean Boot


Even today, Portugal 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 traditionally 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 your soles 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. 


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Astorflex Greenflex


Astorflex Greenflex 
 

After six generations of doing the same thing, you get pretty damn good. That’s why we flew to the home country of Michelangelo and da Vinci to meet the long-toiling Astorflex artisans. From their factory in Northern Italy, they’ve created the Huckberry exclusive Greenflex. These men’s chukka boots are made from leather conditioned by combining water, oak bark, powdered mimosa, and a 30-day wait. The result is a soft, waxy leather that’s also environmentally friendly. Over a natural rubber sole, it’s the same silhouette that WWII desert soldiers wore and Steve McQueen made into a menswear icon. 


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Rhodes Felix Chukka


Rhodes Felix Chukka


“Essential” is a word that gets thrown around a lot in men’s gear, but if the shoe fits, then you should be wearing the Rhodes Felix Chukka. Some of the best men’s dress boots out there, these chukkas are made from premium calf leather that can pair with a suit just as easily as your favorite pair of worn jeans, elevating them both. When there’s a chill in the air, your feet won’t feel it, thanks to a thermal-insulated insole and comfy anti-shock foam layer. Their studded rubber outsole is super grippy, and yet when it finally wears through, you can easily replace it via your friendly neighborhood cobbler. Handcrafted by Portuguese bootmakers with decades in the craft, these men’s chukka boots are the easiest decision you’ll make this fall. 


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Astoflex Bitflex


Astorflex Bitflex
 

Handmade in Northern Italy by a sixth-generation family of shoemakers, it’s not surprising that the Astorflex Bitflex is one of our favorite men’s Chelsea boots. Its beeswax nubuck leather, produced through an environmentally safe process, is soft and supple and ready to go the distance. Speaking of distance, that’s where this boot excels thanks to an ergonomic footbed and a pillowy natural crepe rubber sole. All of this, plus in a style that everyone from the Beatles to Kanye have made iconic. 


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Tricker's Stow Country Boot


Tricker’s Stow Country Boot


If you’re looking to add some Peaky Blinders style to your closet, look to the Tricker’s Stow County. In operation for over 190 years, Tricker’s Northampton factory is the oldest shoe factory in England and has welcomed and outfitted British royalty. With a heavy brogue look and hardy Goodyear welt, these men’s dressboots are made to class up a pair of jeans or finish off your 3-piece wool suit. Lace up a pair of Tricker’s and Tommy Shelby won’t have a chance against you.


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Yuketen Eric Boot


Yuketen Eric


Known originally for their mocassins, Yuketen took their meticulous craft and delved into boots, making a boot we love for a night out, the Eric. Handcut and benchmade in Mexico, the Eric takes a classic American work boot style and dresses it up with suede leather and a slight heel lift. Want to take them out into the backwoods instead of out on the town? Not to worry, as these are finished off with hardy Goodyear stitching and a Vibram sole that will last for years.


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Viberg Service Boot


Viberg Service Boot


Viberg’s most popular model, the Service boot, is an updated interpretation of their original work boot, designed by founder Edwin Viberg in 1931. Made from Italian cowhide leather, these will develop a classic patina over time that will keep these boots uniquely yours. Viberg includes a leather care kit, multiple pairs of laces, and dust covers for each boot with every pair, so you’ll be prepared to keep these looking tip-top from the moment you take them out of the box. 


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>>Next: Best Men’s Chukka Boots
 


 

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