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The 8 Best Men’s Chukka Boots To Wear Right Now

Best Mens Chukka Boots 00 Hero

When it comes to footwear, there are a handful of options that can allow you to take on the highly-formal world, while still being able to dress them down for a day in the city or the beach. One of these options is the chukka boot — a versatile boot born in the desert sands that’s since become something of a fashion staple, following its debut during WWII. Below, we’ll take you through a handful of our favorite offerings from the footwear world, while annotating what makes each unique model special. So, without further adieu, let’s dive into our best men’s chukka boots guide.

Best Chukka Boots Breakdown

What are chukka boots?

Chukka boots were originally worn by British soldiers during WWII and became popular casual wear shortly after, especially across the pond. They’re made of leather, usually with calfskin or suede uppers, and have either rubber or leather soles depending on how casual they’re meant to be. The other key features are the open lacing strung through two to four eyelets.

Chukka Boots or desert Boots?

Sometimes chukka boots will be referred to as desert boots, a silhouette from British shoe manufacturer Clarks based on a South African shoe. Some boots may take inspiration from the design, but in order to be considered desert boots, they need a crepe rubber sole and (usually) a suede upper.

Styling your chukka boots

Chukka boots are very similar to Chelsea boots because they’re durable casual staples that can match comfortably with a suit or a pair of jeans (most of the time). Some variants may lean harder toward a casual or professional style, but you can never go wrong with some chinos and a nice button-up shirt.

Clarks Desert Chukka Boot

  • The original desert boot
  • Quality leather
  • Takes some research to get your size right

The Classic: Clarks might just be one of the most recognizable names when it comes to style-savvy desert boots. So recognizable, in fact, that its very own chukka model is called the “Desert Boot” — demarcating its progenitive prestige, and its genre-defining presence. This versatile variant is an all-original silhouette from the brand’s earliest days, and as such, it boasts a high-quality premium oak nubuck leather upper, contrasting stitching, and a signature crepe sole, paying homage to the bazaar-found footwear that was so popular during its initial run. Over the years, the Desert Boot has become a favorite of off-duty army officers and other military personnel, but these days, it’s a must-have style staple for any guy with a lick of fashionable inclination.

J.Crew 1990 MacAlister Boot

  • Made in Italy
  • Stitched-out welt construction
  • Runs wide

The Best Casual Boots: A timeless ethos is something J.Crew and chukka boots have in common, so it’s not surprising that the former’s take on the WWII-era steppers embraces the silhouette’s heritage. The shopping mall staple’s handsome MacAlister Boots are made in Italy, using locally sourced suede to compose the buttery smooth upper, then finished with stitched-out welt construction and rubber wool for tradition’s sake.

Thursday Boots Scout Chukka

Thursday Boots Scout
  • Versatile style
  • Midsoles form to your feet
  • Heels may be high for some

The Best Formal Boots: Thursday Boot Co. has been on the up and up when it comes to the creation of iconic men’s boots. While the company isn’t necessarily as old, or as experienced, as its counterparts, it more than makes up for that (perceived) weakness by offering buyers well-informed essentials at a fraction of the price of premium models. That doesn’t mean that Thursday throws construction, dependability, and style to the wayside, however. The Scout, for example, is a perfect representation of well-contrived fashion, adopting an ultra-sleek chrome leather exterior, stitch-out attributes, and a fully-lined glove-leather interior, promising enhanced comfort for its wearer. Each model also utilizes a shock-absorbing Poron insole, giving the shoe antibacterial properties that complement its formative cork-bed midsection. To round things out, each of Thursday’s footwear pieces is handcrafted with the utmost attention to detail, ensuring that you’ll receive a top-of-the-line shoe, without paying top-of-the-line prices.

Astorflex Brownflex Chukka Boot

Astorflex Brownflex Chukka Boot
  • Handmade in Italy
  • Lined with leather
  • Can be slippery on wet surfaces

The Best Boots Overall: Taking inspiration from the classic desert chukkas of WWII and using uber-soft European leather, Astorflex took this staple silhouette to new heights. The Brownnflex Chukkas are handmade by a sixth-generation workshop in Italy and sit on natural crepe rubber soles that are likened to “walking on a cloud,” deeming them comfortable for you and the soil you walk on. Best of all, they’re available in four options with either suede or nubuck, so you can choose the right one for any outfit — needless to say, you can’t go wrong with any of them.

Sanders Hi Top Chukka

  • English heritage brand
  • Made in the UK
  • UK sizing

The All-Arounder: Sanders, like Clarks, is an English heritage brand that knows its way around a pair of desert boots. The brand’s classy Hi Top iteration is as traditional as it gets, allowing you to bask in the idea of wearing timeless shoes that are bound to last you a while — that’s the epitome of longevity. This option is available in several styles, including the pictured Dirty Buck Suede and additional, more vibrant hues.

Red Wing Heritage Weekender Chukka Shoe

Red Wing Heritage Weekender Chukka Shoe
  • Outsoles are good for wet conditions
  • Comfortable footbed
  • Takes some time to break in

The Upgrade: If you’re a fan of men’s footwear and you haven’t heard of Red Wing Heritage, we’ll have to question your devotion. Not only has the brand been around for over 100 years, but it’s also become one of the most prominent names in the industry, thanks to its commitment to classic styles. While Red Wing certainly specializes in rough and rugged outdoor boots, the brand has a more refined side, which is exemplified through its Weekender. This chukka-styled silhouette was built for off-the-clock wear, and reminisces the fashion icon in its earliest days, while still including the brand’s recognizable stitch-down construction, ComfortForce footbed, and shape. On its exterior, a copper leather construction, courtesy of S.B. Foot Tanning Company, provides a timeless look, overall, but also brings water, stain, and perspiration resistance to the table for interested buyers. To top things off, each model is crafted right here in the USA.

Rancourt and Co. Blake Chukka

  • Antique brass eyelets
  • Burnished by hand
  • Socks are recommended while breaking them in

The Best American-Made Boots: Rancourt’s Blake Chukka is another more timeless model. Instead of adopting a plethora of modern traits and components, the brand stays true to the tried-and-true blueprint set forth by its genre’s initial examples, including a natural leather midsole, a Horween Bulldog burnished cowhide upper, and antique brass eyelets. That doesn’t mean that it’s afraid of change, though. To complement the shoe’s braided wax cotton laces and unlined interior, a Reltex Lactae Hevea crepe sole has been introduced, providing enhanced comfort, durability, and traction for stubborn wearers who refuse to let the past slip away.

Quoddy Kennebec Chukka

  • Extra ankle coverage
  • Cushioned insoles
  • Runs small

The Best Moccasin Style Boots: It’s difficult to create a respectable footwear list without the inclusion of Quoddy. As such, we’ve decided to reveal one of the brand’s best-kept secrets: the Kennebec chukka. This hybridized boot/shoe combo is a delightfully-designed model that’s remained under the radar for a vast portion of the market, and we’re not sure why. It boasts a true moccasin construction, lacquered eyelets, rawhide laces, and a bespoke Vibram sole specially developed for Quoddy. If that doesn’t tell you something about the brand’s quality, construction, and performance, then we don’t know what will.

The Best Lightweight Jackets for a Versatile Look

Best Lightweight Jackets 00 Hero

Your new chukka boots are undeniably durable and stylish, and you’ll want something with the same qualities to complete your look. So check out our best lightweight jackets guide to complement your boots.