Chukka Boots: The Best Chukka Boots for Every Occasion

Picture it now: You’ve got your footwear collection lined up like ducks in a row, all set to select your new favorite pair of shoes for the day’s pursuits. But if said footwear collection doesn’t have at least one pair of chukka boots, you’re not doing it right — yet. If you’ve found that your footwear rotation is missing this iconic menswear staple, well, allow us to set the record straight.

You need chukka boots, and you need ’em now. The chukka boot is among those crucial footwear styles a man has simply got to have. It’s more dressed up than a pair of canvas sneakers (which, by the way, you should also have!, but they’re a step down — pun intended — from dress shoes. Plus, they’re a change of pace from rugged rubber boots (say that five times fast). In short, a pair of the best chukka boots are kind of like the jack-of-all-trades in most instances for your wardrobe. Granted, you can’t wear chukka boots to the beach or the boardwalk — nor would you want to — but you can wear chukka boots just about anywhere else you can dream up. That, my friends, is a winning set of boots for the modern man.

As luck would have it, this essential pair of boots also happens to be easily wearable in any season, practically. Sure, you might lean towards summer-weight canvas sneakers or leather loafers from time to time, but when you want to step out in causally rugged style, day or night, the right pair of boots can certainly pass muster. It helps that this iconic style has plenty of heritage and history built right in.

Chukka boots, like all great menswear innovations — like the henley shirt, worn by British sportsmen, or the field jacket, worn by the military — find their roots in true functionality. Chukka boots are perhaps more commonly known as desert boots, worn in the desert by British soldiers in World War II. So, yes, a desert boot is a form of a chukka boot, but desert boots usually feature a soft crepe sole and an unlined design. Chukka boots can be sturdier, made from hard-wearing leather and sometimes featuring a studded rubber outsole.

You’ll see these classic men’s boots referred to by either name out in the menswear wilds today. Overall, we say it’s best not to overthink it — if you like what you see, then we’re all for you getting those boots on your feet ASAP. Chukka boots, like we mentioned earlier, are truly a jack-of-all-trades type of boot. If you want boots you can wear with jeans to the office, you want chukka boots. If you want boots to wear with a cotton suit, a la James Bond in Spectre, well, chukka boots are the way to go.

And if you want boots that can do a little bit of everything — as in, boots to wear to the office, then to the bar, then to a rock concert –well, the right pair of chukka boots can do that, too. A word to the wise: Keep your denim dark and slim, make sure your shirt is a rougher, more rugged material like chambray, and make sure your chukka boots are built with rugged leather. We’ve got just the proper pair in mind. Read on to find out more on our favorite chukka boots. In the meantime, here’s how to shop for chukka boots.

What to Look For When Shopping for Chukka Boots

  • Material: This goes hand-in-hand (or step-by-step?) with what we mentioned above as far as the utility of chukka boots is concerned. Some chukka boots are made with lightweight suede, while others are made with durable, rugged leather. We say that you need a pair of each, at least, in your rotation, but it all depends on how you intend to wear your chukka boots. If you want a pair that can do a little bit of everything, look for chukka boots made with tough leather. Again, who says you have to stop at just one pair, though?
  • Design: Here’s another deep dive into what we talked about earlier. Some chukka boots are built with a tough outsole that’s not all that different from your favorite leather work boots. Others still feature that soft crepe sole we mentioned earlier. For maximum durability, dependability and traction, we’re all in favor of chukka boots that feature both a sleek build and a hard-wearing outsole. You’ll find your new favorite pair of men’s boots below, we guarantee it.
  • Price: As far as menswear essentials are concerned, we’re all about getting the most bang for your buck. If you want chukka boots that give you top quality for top dollar, it’s best to look for a versatile pair that you can wear day in and day out. If you’ve been keeping up with our guide to boots, that means they’re typically going to be made of leather atop a studded rubber outsole for plenty of all-day wearability. And just like that, you’ve maximized the return on your investment. Still with us? Great.

With that trifecta of tips in mind, the time is now to revamp your footwear rotation with a pair of the best chukka boots. Here are the best men’s chukka boots we’re digging at the moment.

The Best Chukka Boots for Every Occasion

Astorflex Greenflex Boots

Astorflex Greenflex Boots

Well, folks. Here they are. These Astorflex boots, made sustainably at a family-owned factory, are truly a gem in the world of hard-wearing boots. And in fact, they’re about the most reliable pair on the market, what with the durable rubber outsole and tough leather construction. Like we said above, versatility and affordability are the name of the game when shopping for chukka boots. And my friends, this pair checks all the right boxes. Plus, you can wear them with chinos or jeans quite easily. Naturally, it’s also a prime time to stock up on other menswear essentials at Huckberry as you peruse the site’s impressive collection of boots. And truly, what’s not to love about that? We can’t think of a single thing. Lace these up accordingly, folks.

Rhodes Footwear Tyler Chukka Boots

Rhodes Footwear Tyler Chukka Boots

We’ll head back to Huckberry for this pick, a truly rugged and tough pair of boots. These are the kind of pair you can wear with pride, especially with other style staples like indigo denim and your favorite henley. These more closely resemble what you might consider classic desert boots, what with the crepe outsole. Plus, they’re made in Leon, Mexico, one of the world’s finest hubs for footwear craftsmanship, so you know they’re worth the slightly more elevated price tag. And of course, the sleek design makes them ever-so-slightly dressy. What we mean to say is that, while we’d shy away from wearing these with a suit, you can certainly rock them with tailored chinos and a navy sweater polo at the office. Give it a whirl and let us know how it goes.

Allen Edmonds Discovery Chukka Boots

Allen Edmonds Discovery Chukka Boots

You very well might have seen Allen Edmonds in your dad’s shoe collection over the years, but trust us when we say the lauded, American-made brand is anything but stuffy these days. They’ve always specialized in classic shoes and boots for men, but they’re doing so with a more modern tilt these days. Take the sustainably made Discovery Boots, which feature a biodegradable toe box and, as Allen Edmonds puts it, an “XL Extralight Sustainble+ sole made with recycled content.” What that means for you is that you can feel great about wearing these pleasingly versatile boots day after day, and we’d wager you’ll want to pair them with everything from light wash jeans to slim tan chinos. They’re just that great.

Brunello Cucinelli Suede Chukka Boots

Brunello Cucinelli Suede Chukka Boots

Who said shopping for chukka boots has to be boring? These suede boots, packed with refinement and plenty of dressy style, are the opposite of boring. They’re downright splurge-worthy, something that we think you deserve when adding to your footwear rotation. In fact, consider that high price tag a sort of incentive to wear the heck out of these dressy boots. We said that affordability is assuredly one of the key factors in shopping for boots, but we’re willing to throw that out the window, if only briefly. We’ll consider these the best chukka boots to buy if you want dressy, sharp style — and if you want a little extra motivation to wear them as you get the most mileage out of your investment.

Cole Haan Osborn Plain Toe Chukka Boots

Cole Haan Osborn Plain Toe Chukka Boots

We keep coming back around to the idea that your boots should be versatile as heck. Wouldn’t you agree? If we’re still on the same page, then this writer would wager that you’re going to like what you see as far as these boots are concerned. They’re durable, they’re well-built, they’re affordably priced and they’re easy enough to wear to the office or out on the town on your next road trip. Throw in the handsome burnished leather and we’d say they go above and beyond what you need in a new pair of chukka boots.

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Beau is Brooklyn-based style and lifestyle writer. He covers menswear, gear, spirits, craft beer and music. When not writing, Beau can be found shopping for vinyl or sipping on a Brooklyn beer.

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