The 6 Best Boots for Men

From durable work boots, to dressed-up Chelseas, to laid-back suede chukkas, these are the essential boots every man should have in his arsenal
October 15, 2019Words by Cody Ernst

Originating around 1000 B.C. within tribes of horse-riding nomads, boots are arguably the oldest, most well-worn men’s footwear in history. Flash forward three millennia and what started out as equestrian foot armor has been honed into many essential, distinct styles that can serve nearly any situation—from getting suited up for the office, to pouring concrete, to exploring the world. Boots are a Huckberry house favorite, so it was tough to decide, but we narrowed our ideal collection down to our favorite boot in each of the six essential styles every man should have in his closet: dress boots, chukka boots, work boots, hiking boots, rain boots, and Chelsea boots. Whichever you’re looking for, read on to find your perfect pair. 
 



The Best Dress Bots: Rhodes Dean Boot
 

The Best Dress Boots: Rhodes Dean Boot


Historically worn by: New Englanders, city dwellers 

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

When we need to look our best, the Dean Boot is our go-to. Every time you thread the laces through the easy-on speed hooks, you'll see the calf leather subtly aging with a handsome patina that makes them more uniquely yours with each mile you put on 'em. And when the miles really start to add up, that hard-earned patina isn't going anywhere—Blake construction means a cobbler will make short work of replacing the sole and you'll be back in your favorite everyday boots in no time. Premium materials, best-in-class craftsmanship, fully resoleable—in other words, this is a pair of boots you can depend on for a lifetime of service.


SHOP 9 BEST MEN’S DRESS BOOTS
SHOP THE RHODES DEAN BOOT

 

 



The Best Chukka Boots: Rhodes Dylan Chukka


The Best Chukka Boots: Rhodes Dylan Chukka
 

Historically worn by: Polo players, WWII Soldiers in North Africa 

Best for: Weekends, everyday wear, travel 

Chukkas, aka Desert Boots, were originally designed to withstand the harshest arid climates in the world. Popularized by WWII soldiers who brought them back home to England from the North African campaign, they’re a sharp-but-casual boot perfect for travel, weekend wear, and even dressing up. And they’ve been immortalized by the likes of Anthony Bourdain and Steve McQueen. For our money, our favorite Chukka Boot right now is the Dylan, by Rhodes. Cut from soft Italian suede, with the natural rubber sole desert boots are known for—they’re so comfortable and handsome, they have “go-to” written all over ‘em. 


SHOP 9 BEST MEN’S CHUKKA BOOTS
SHOP THE RHODES DYLAN CHUKKA

 



The Best Work Boots: Truman Service Boot
 

The Best Work Boots: Truman Service Boot


Historically worn by: Tradesmen, soldiers, Indiana Jones 

Best For: Hard work, double shifts on your feet, outlasting the competition  

When asked to picture a boot, a work boot is probably what comes to mind. Rugged, ankle-length, lace-up, leather. Between bootmakers in New England, the Midwest, and Pacific Northwest, the USA is a mecca of handcrafted, ultra-durable work boots that still live up to the standards of the old school. With so many to choose from, we decided to highlight one of the most rugged in our arsenal—the Truman Service Boot in an exclusive Tan Coach leather. 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—so, like a quality leather boot should, they’ll custom mold to your feet as you wear them and are made to wear and repair for life. 
 

SHOP 8 BEST MEN’S WORK BOOTS
SHOP THE TRUMAN SERVICE BOOT

 



The Best Hiking Boots: Danner Vertigo 917
 

The Best Hiking Boots: Danner Vertigo 917
 

Historically Worn by: Thru-hikers, mountaineers, Yvon Chouinard 

Best for: Multi-day treks, unpredictable terrain, comfort 

Built to withstand the elements and keep you comfortable throughout long, trying days on your feet—hiking boots first became cult favorites amongst outdoorsmen in the 1970s and ‘80s, who had theirs shipped over from mountaineering companies in Italy. Nowadays, you just have to look around to see that hiking boots have exploded in popularity, and can even border on stylish if you know what to wear ‘em with. Of all the hikers we’ve worn, Danners hold a special place in our heart. Tested by Pacific Northwest loggers, proven in WWII, and made famous by thru-hikers—they’re basically the archetypical American hiking boot. Danner designed the Vertigo 917 with the urban explorer in mind. Outfitted with all the technical details that make Danner’s trail boots among the most popular but with a lightweight sole and twin gores for easy on and off, the Vertigo is ready for any urban or outdoor adventure you find yourself on.


SHOP 11 BEST MEN’S HIKING BOOTS
SHOP THE DANNER VERTIGO 917
 



The Best Rain Boots: Xtratuf Leather Ankle Deck Boot


The Best Rain Boots: Xtratuf Leather Ankle Deck Boot
 

Historically worn by: Fishermen, farmers, Alaskans, Brits 

Best for: Inclement weather, stormy seas, walking to the office through slush 

When you think “rain boots,” you probably picture the type of knee-high, green rubber boots worn by farmers on the job. We thought the same, until we went to Alaska and met the team at Xtratuf. What cowboy boots are to Texans, what flip flops are to Hawaiians, Xtratufs are to the residents of our 49th state. Why? Because Alaska has some of the wettest, most treacherous land on the continent and these boots in particular are tough enough to keep you dry and on your feet no matter how screwy the weather gets. 


SHOP 6 BEST MEN’S RAIN BOOTS
SHOP THE XTRATUF LEATHER ANKLE DECK BOOT
 

 



The Best Chelsea Boot: Rhodes Chelsea


The Best Chelsea Boots: Rhodes Huxley Boot


Historically Worn by: The Beatles, Bob Dylan, City dwellers 

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

The humble Chelsea boot has a wild history—invented during Victorian times as a durable riding boot, their easy slip-on design gained popularity over the years and wound up gracing the feet of rock ‘n roll legends like The Beatles, The Rolling Stones, and Mr. Bob Dylan himself. With their convenient design and dress up or down versatility, we’re betting they’ll stick around another couple hundred years. Our pick in this category is the new Chelsea from Rhodes. Handmade and fully leather-lined, these beauties are a hell of a good deal for the price—and are fully resoleable for life.
 

SHOP 8 BEST MEN’S CHELSEA BOOTS
SHOP THE RHODES HUXLEY BOOT

 

 



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