Stylish and rugged—chukka boots are one of the best footwear options for men. Few other options can rival the versatility of chukkas. They can be paired equally well with jeans and a t-shirt as with a casual suit.
This article will explore what is and what isn’t a chukka boot and examine the boot’s unusual origins. After that, we’ll look at the best chukka boots to buy in a budget, mid-level, and “grail” options for men in the market for a pair.
Next, we will go through the pros and cons of chukkas in each color, followed by a quick Q&A. We’ll end by reviewing a few specific examples of what to wear with chukka boots.
Let’s get started!
Best Chukka Boots to Buy
If you’re considering buying a pair of chukka boots, be sure to check out the carefully curated selection below. I’ve included only options with solid reviews that are worth further inspection. As full disclosure, I have only personally tried a few of these boots.
I do want to mention that there’s a reason why the chukka boot lands so high in our list of Men’s Shoe Essentials.
Before getting into our picks, be sure to check out the Huckberry Chukka Boots Collection which gives you tremendous variety to choose from.
Budget ($40-$100)
Clarks Bushacre 2
The Clarks Bushacre 2 is the the more affordable version of the Clarks Desert Boot. You can find it for under $60 on Amazon in a myriad of colorways from leather to suede.
The primary difference between the Clarks Desert Boot (which Khoi owns and has reviewed) and the Bushacre 2 Chukka boot is that the former features an unmistakable crepe sole while the latter has a hard and smooth rubber sole.
Nisolo Daytripper
Nisolo’s Daytripper chukka boot currently comes in 2 colorways of tobacco and waxed brown. It’s Nisolo’s first ever boot in their footwear collection. It’s definitely a sleek, smart casual leaning boot with the classic chukka silhouette.
In addition to the high quality leather, it’s comfortable to boot with a 5-layer memory foam insole with built in arch support. It also features a waterproof outsole that provides comfort and extra grip. And if sustainability is important to you, the leather upper is Leather Working Group Certified. A win win if you ask me.
As for the current price, the boots normally run for $200, but is on final sale for $100. And you can get an additional 25% off w/ code SPRING25.
Mid-Level ($100-$250)
Thursday Scout Chukka
Khoi (Gentleman Within’s founder) has a long-term review of 3 pairs of Thursday Boots, namely the President, Captain and Duke styles. He has a pretty good idea of how these boots hold up over the long haul.
The Scout Chukka comes in at a competitive $160 and 9 different colors/styles to choose from. What’s great about Thursday is that all of their boots come equipped with a Goodyear welt which means that they’re easily resoleable once the soles are worn down.
Timberland Redwood Falls Chukka
If you’re looking for a comfortable, rugged chukka boot option, look no further than the Timberland Redwood Falls chukka. Appearance wise, the Redwood Falls has that classic Timberland rugged style with metal grommets, thick L7 multi-directional lugged outsole with contrast stitching and the Timberland logo embossed on the side of the ankle. It also has premium leather than you can expect from the Timberland brand.
Additional highlights include an extra cushioned interior, waterproofing, OrthoLite footbed with a steel shank for arch support and Gripstick rubber outsole. Perhaps the best part is that this premium pair of boots currently comes in at an affordable $135.
Grail ($250-$400)
Frye Bowery Chukka
Frye is a heritage brand that’s been around for over 150 years. This pair of Bowery Chukkas come in sizes 7-14 in the versatile and stylish tan colorway. The boot has a Goodyear welted construction with oiled vintage leather.
If you’re looking for something a bit more on the rugged end of the spectrum, but stylish as ever, the Bowery chukka is a fantastic option. While it normally retails for $378, it’s currently on sale for under $230 which makes it amazing value.
Allen Edmonds Chandler Weatherproof Chukka
Since you’re on this page then more than likely you are familiar with the AE brand. Synonymous with men’s leather footwear, Allen Edmonds has been in the game for over 100 years now, founded in 1922.
The Chandler Chukka has a classic lace-up chukka boot style and silhouette. It’s equipped with a 360º storm welt, weatherproof construction too keep your feet comfortable and dry in wet elements. The boot also has Dainite rubber outsoles for great traction and their proprietary CustomCork insoles that mold to the shape of your foot.
It’s a relaxed fit with a slightly roomier feel. This pair can easily be dressed up or dressed down and it’s built on AE’s 1757 footwear last, the same style used for their bestselling Higgins Mill boot.
It rarely goes on sale, but AE is currently running one which drops this slick chukka down from $495 to $379, which is tremendous value.
» You Might Like This Guide on the Best Sock Brands for Men (10 Quality Pairs for Every Activity).
Difference Between Chukka, Desert, and Chelsea Boots
It’s easy to confuse chukka, desert, and Chelsea boots. While all three are types of ankle boots, each has its distinct differences.
What are chukka boots?
Chukka boots are ankle-high leather boots. These open-laced boots traditionally have two or three pairs of eyelets. Chukka uppers are typically sewn from two pieces of calfskin or suede.
The classic Clarks Desert Boot in Beeswax.
From cheap cemented soles to more durable (and more costly) stitch-out construction, you’ll find that chukka sole material and construction vary widely between different brands and models.
Related: You might like this Clarks Desert Boot Review.
Chukkas vs desert boots
By this point, you might be thinking, “Doesn’t that description also apply to desert boots?”
Great question! In many ways, yes—chukkas and desert boots are very similar. In fact, even in the fashion industry, for many people, the names are interchangeable.
That said, there is, technically, a difference between chukkas and desert boots.
Desert boots always have a crepe sole. Chukkas, on the other hand, can, but don’t always, have crepe soles.
Crepe rubber is a type of soft, squishy rubber that, when used for soles, gives the wearer an incredible grip in slippery conditions. It also gets very dirty.
If you’re considering getting a pair of shoes or boots with crepe soles, you should know that, due to crepe being a soft material, they will likely wear out faster than shoes with hard rubber soles.
Besides their distinctive sole, desert boots uppers are suede. However, chukka uppers can be made from suede, calfskin, or other natural or synthetic materials.
Also, desert boots and chukkas differ in color. Desert boots are usually sand-colored, while you can find chukka boots in almost any color you can think of.
Can you tell which one is a desert boot?
Did I lose you? You don’t have to worry about the details. The main point is that the term “desert boots” refers to a specific type of chukka boot.
In other words– all desert boots are chukkas, but not all chukkas are desert boots.
Chukkas vs Chelsea boots
Chelsea boots are another type of ankle boot. Unlike chukkas, Chelseas don’t have laces. Instead, they have a band of elastic around the ankle that allows the wearer to put them on and take them off easily.
I’ll give it to you this time. The chukka boot is on the left.
In my opinion, the sleek profile of Chelsea boots makes them just a bit more formal than chukka boots.
History of the Chukka Boot
Chukka boots, or boots like them, have been around for a long time.
Chukka boots were “discovered” by the Western world during WWII when soldiers in northern Africa noticed that the local’s footwear was better adapted to the desert climate than their military-issued boots.
It turns out the local traders’ boots were adapted from traditional South African veldskoen (A word literally translated from Afrikaans as “skin shoes”).
A modern interpretation of traditional “vellies” (veldskoen)
Tradition holds that the soldiers instructed cobblers in Cairo’s famous Khan el-Khalili bazaar to make shoes inspired by the locals’ kicks. Thus, the desert boot was born.
The soldiers were delighted to discover that their new desert boots were terrific in the sandy deserts of Africa. Their light construction helped keep the men nimble.
Their open-lace construction helped to keep sand from pouring in, and the crepe sole provided much-needed traction on the fine sands of the Sahara.
Recognizing the potential of this exotic boot style, civilians in the West continued to experiment on the design of the desert boot to adapt it to the urban man’s wardrobe.
The unique Tripoli Chukka from Taft. (Check out GW’s Taft Boot Review)
Thus, in the space of just a few short years, vellies, after being reimagined and reinvented, made their way out of traditional African communities and onto the red carpets of Hollywood.
Even today, chukka boots continue to change and adapt as brands continue to innovate with new styles, materials, and construction methods.
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Color Me This (Chukka Colors)
As you can see from the list above, there are many different styles of chukka boots. Likewise, they come in a wide array of different colors.
Let’s explore the pros and cons of each color of chukka boot.
Black chukkas
Black chukkas might be a good option for chukkas on the more formal end of the spectrum.
Black Williamsburg Chukka from Allen Edmonds.
However, they’re not the most versatile color for chukkas. That said, if your wardrobe consists of mainly dark, monotone pieces, you might get a lot of wear out of black chukkas.
Even then, I’d probably still recommend opting for a pair of gray chukkas over black.
Dark brown chukkas
When it comes to chukkas, dark brown is probably going to be your versatile color choice. Of course, versatility will depend on your own personal color palette.
Unless you wear mostly black, dark brown chukka boots will go with most things in your wardrobe.
The example above is an ultra rich burnished dark brown that’s versatile as ever.
Tan/sand chukkas
Tan or sand-colored chukkas are the next most versatile chukka color options.
Once again, these will go with almost anything in your closet.
Gray chukkas
I own a pair of gray chukka boots. I’m surprised just how much I wear them.
Gray Suede FTW!
The great thing about gray boots is that they work just as well with black jeans as they do with tan chinos.
Blue chukkas
Blue boots? I know, at first it sounds weird, but hear me out.
Navy or midnight blue suede chukkas are a great way to dip your toes into trying non-traditional footwear colors. While certainly unusual, they don’t stand out as much as you might think they would.
Since chukkas already straddle the line between formal and informal, suede is a fantastic choice for chukkas.
With its napped texture, suede is a more informal fabric than smooth leather.
Wearing a pair of midnight blue suede chukka boots with a pair of great-fitting blue jeans is a great laidback look.
Chukkas in other colors
Chukkas in unusual colors such as white, burgundy, green, or even yellow are going to be harder than the options above to fit into your wardrobe.
Too much? Only for the bold.
Unless you already have a sizable shoe collection, I’d advise getting chukkas in uncommon colors.
How to Wear Chukka Boots (For Men)
Next, let’s shift gears and explore specific examples of how to rock chukkas with style.
How to wear chukkas with jeans and a t-shirt
Instead of wearing sneakers with jeans and a t-shirt, switch things up and throw on a pair of chukkas.
Go for a solid-colored classic tee and fitted jeans or chinos.
Adding a watch or bracelet will elevate the look.
How to wear chukkas with a bomber jacket
Ryan Reynolds, I feel like he’s trolling us at every turn. (his casual style though
)
How to wear chukkas with chinos and a button-up
Moving on, wearing cream or tan chinos and a button-up shirt is still casual but a step up in formality.
Try wearing classic desert boots with a watch and a matching belt. The belt doesn’t have to be suede, but it should be a similar shade of brown. Opt for a casual dive watch, and you’re good to go.
Alternatively you can dial up the formality with a tucked in white dress shirt and dark brown braided belt with dark brown chukka boots. It’s hard to go wrong here.
How to wear chukkas with a field jacket
For this next look, we’ll start with an olive field jacket. Find yourself a pair of dark brown leather or grey suede chukkas with a medium/thin sole.
For the pants, you have options, but try to stick with subdued colors, such as tan, brown, grey, or navy, or even burgundy.
For an even smarter look, leverage the power of layering by wearing a charcoal grey v-neck sweater over a collared shirt.
If you’re a watch guy, a field watch with a brown leather strap would be a great choice.
I can hardly think of a better fall outfit.
How to wear chukkas with a leather jacket
Gray suede or brown chukkas pair excellently with a black motorcycle jacket. For a subdued, monotone look, you could wear black or dark blue jeans and a light gray shirt underneath the jacket.
If you have a brown leather jacket, go for, you guessed it, brown leather chukkas of a similar shade.
Alternatively consider wearing gray wool dress pants, a patterned shirt, and a casual knit tie for a smart casual occasion.
How to wear chukkas with a crewneck sweater
Chukka boots are right at home with a casual fit like this. You can pair the laid back grey suede chukkas with a navy crewneck sweater. It’s an ideal fit for early spring or early fall.
If you’ve got a pair of olive trousers in your closet, this addition jives well with the overall earth tone color palette.
How to wear chukkas with a navy blazer
Chukkas and the navy blazer pair really well together. That’s probably because both pieces play similar roles in your wardrobe as they each span the gap between ultra-casual and smart casual.
Wear white jeans, a blue chambray shirt, and light brown leather chukka boots for an elevated summer look. If you want, throw in a fun pocket square or bracelet.
Related: You might like this How to Wear a Navy Blazer.
For a more formal occasion, wear a creased trousers, dress shirt, and tie.
How to wear chukkas with a suit and tie
Yes, you can even wear the ever versatile chukka boots with a suit and tie, but you want to be careful here. You’ll definitely want to wear a style closer to the “more formal” range from the infographic above.
But of course style rules as with anything are meant to be broken. You can feel free to experiment with a lighter colored sand suede chukka with a light gray suit, oxford cloth button down and dark tie. You can even throw on a casual vest to dial up the IDGAF, cool vibes.
Frequently Asked Questions About Chukkas
And now, I’ll answer some common questions about chukkas.
How Formal Are Chukkas?
Due to their utilitarian origins and rugged construction, most chukkas are casual.
I say “most” because chukka boot formality depends largely on the boots’ construction and materials.
Yes, there are even ultra-casual chukka sneaker.
A sleek dark brown, full leather chukka with a leather sole is going to be more formal than a sandy-colored suede chukka with a crepe sole.
Can you wear chukka boots with dress pants?
Chukka boots are an excellent choice of footwear to pair with dress pants.
Nothing says “corporate drone” like cheap, boxy shoes. Choosing to wear high-quality, interesting shoes or boots to the office can provide some visual interest to an otherwise bland outfit. Chukkas are especially great for this because they are generally somewhat uncommon.
If you’re wearing chukkas to an event that leans more formal, go for smooth leather chukka boots with some shine to them.
Can you wear chukka boots with a suit?
You can even wear more refined chukka boots with a suit. However, it has to be the right suit and the right pair of chukka boots for you to pull off the look.
As a rule of thumb, choose chukkas with a thin leather or rubber sole in natural, conservative colors to wear with suits.
While you can wear suede chukkas with rubber soles with a casual summer linen suit, they will definitely be too casual for a business suit.
Of course you can pull it off.
For a more formal dark wool suit, choose leather-soled calfskin chukkas in dark brown or black.
For formal events (black-tie optional and up), chukkas simply won’t cut it. Instead, wear a quality pair of black leather oxfords.
Can you wear chukka boots in the winter?
Chukka boots aren’t ideal for winter — at least not the harsh northern winters that I’m used to. (There’s a reason they’re not called “tundra boots”).
That said, you can wear chukkas during the cold months of the year; just be sure to avoid deep snow, slush, and salt as much as possible.
Even suede chukkas aren’t out of the question.
Contrary to what you may have heard, suede can be worn year-round. Just make sure you waterproof suede chukkas before their first foray out “into the wild.” Reapply the waterproofing agent of your choice regularly (as frequently as once a week during wet months).
Chukkas weren’t designed specifically with cold and wet conditions in mind. When the mercury goes south, you’re better off wearing boots made to deal with winter weather.
Final Thoughts
Whew! We covered a lot of ground.
Let’s review where we’ve been. We explored the difference between chukka, desert, and Chelsea boots, had a crash course in chukka history, and looked at several places to buy these versatile boots.
We’ve also examined chukkas in different colors, answered common chukka-related questions, and finally, looked at specific examples of how to wear chukka boots with style.
Chukka boots are an underutilized footwear option that every man should consider wearing.
I hope that you found this guide helpful. For further reading, check out this complete guide on boot styles for men.
Do you have any favorite pairs of chukka boots?
Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.
Looking forward to seeing you in there.
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