A Guide to Chukkas and Desert Boots (featuring Clarks)

As promised in my earlier Fall and Winter Boots: My Favorite Styles post, I'm rolling out a guide for each of the featured boots with background information and examples of how to wear them.

Kicking off this series is the most comfortable boot on the block – the Chukka.

Chukka Boots

All Desert Boots are Chukkas, but not all Chukkas are Desert Boots. Confused? Good, let me explain.

The terms Chukka and Desert boot are sometimes used interchangeably, but there are a few differences.

To briefly explain, a chukka is a two or three eyelet ankle boot that’s made of two pieces of leather (a front piece and a back piece), has a plain toe, and a leather sole.

Desert boots are a type of chukka and share the same ankle height and number of eyelets, but have a natural crepe rubber sole and are more casual in both materials and construction.


Chukkas can be found in a broad spectrum ranging from quite formal to extremely casual.

On the left, you can see an example from Ralph Lauren (similar). Note the smooth leather, sleek profile, pointed toe, and leather sole.

This makes for a boot that can be worn to the office during the day, out to dinner in the evening, and casually on the weekend.

On the right is the famous Clarks desert boot. Note the suede uppers, flat laces, rubber sole, unfinished edges, and wider profile.

All these characteristics make for a shoe that is best paired with casual attire.


There are many theories about the actually origin of this boot style but for simplicity, let's just say that the desert boot style was adopted by British soldiers in the Western Desert Campaign of WWII.

Nathan Clark, of Clarks Shoes, first noticed this style on a trip to Burma. He introduced the Desert Boot to America at the 1950 Chicago Shoe Fair.

They then became popular with beatnik generation and mod movement of the 1950s and 60s.

My Experience

These are the most comfortable shoes I've ever worn!

Seriously, they’re the only shoe that doesn’t force my foot to conform to some cruel and unnatural shape.

Desert Boots are so comfortable, in fact, that the first time I laced them up, I expected to take a step and walk right out of them.

To my surprise, they stick to your feet like glue, moving with you perfectly. It actually took quite a while to get used to  their lack of interference.

This boot is comfortable in the way that your house slippers are comfortable – no ankle support, motion control, steel shank, or arch support here. Just good looks and pure comfort.

How to Wear

Desert Boots are your new sneakers. Really, leave the Nikes in your gym bag. These are just as comfortable, lace up without fuss, and look great with any casual outfit.

Desert boots look great with jeans, casual trousers, and I’ve even seen some fashion forward people wear them with shorts (experts only).  Below are a couple of potential looks that pair nicely with desert boots.

Cotton Trousers and a Fitted Button Up




Raw Denim and an Oxford Cloth Button Down




When shopping for chukkas, you'll encounter a wide range of prices depending on type and construction of the boot.

One hint though: if you're opting for a desert boot, there's no reason to look elsewhere beyond Clarks.

That said, here are some great options from cheapest to most expensive:

Low – Clarks Original Desert Boot

Mid – Cole Haan Cambridge 

High – Allen Edmonds Dundee Cordovan


So how do you like to rock your chukkas?  Dressed up or down?  Let me know in the comments below!

You Might Also Like


  • Reply
    February 3, 2015 at 6:14 am

    Can you recommend a chukka boot that works for those with narrow feet? (The Clarks are not narrow.)

    • Reply
      February 3, 2015 at 8:02 pm

      The clarks are quite wide, as are most other casual shoes. Your best bet would be to move up to the dress shoe category because they’ll actually offer you a choice of widths. I purchase from and recommend Allen Edmonds. Also, anything from Cole Haan or To Boot New York is always too narrow for me so that’s another option to consider.

  • Reply
    February 13, 2015 at 4:24 pm

    Thanks for the response! I just tried a pair of the AE Gobi in the narrow size and they fit me well. For shoes to kick around in the cost is a little prohibitive but they may be the ones for me. I have never worn a Cole Haan so I will give those a try.

    • Reply
      February 15, 2015 at 11:05 pm

      The price is little steep for a casual shoe. They’re great quality and Allen Edmonds frequently has 20-40% off sales. Hope you find something that works for you.

  • Reply
    October 2, 2015 at 7:53 pm

    I have the Bushacre 2 (DB’s with synthetic sole) and am looking at getting the original DB’s. What color did these start as? Beeswax? Thank you in advance and keep up the great content!

  • Reply
    October 22, 2015 at 2:54 pm

    I really like the desert boots and own other Clarks, great shoes. But the desert boots feel like they would need breaking in or an extra insole. Was that your experience at all?

    • Reply
      October 22, 2015 at 3:18 pm

      My pair in beeswax leather didn’t require any break-in at all and the suede ones are even softer. On the topic of insoles, I don’t use any as I find the squishy crepe rubber sole does more than a good enough job absorbing shock and providing all day comfort. It’s true that they don’t offer much in the way of arch support, though. So if that’s important to you, you could consider an insole. I sized down to an 11 1/2 from my normal 12, but if you want to add an insole get your normal size to make sure you have enough room. As a final note, these are probably the most comfortable pair of shoes right out of the box I’ve ever worn.

  • Reply
    October 22, 2015 at 10:18 pm

    Thanks for the response!
    Cool site .

  • Reply
    November 11, 2015 at 3:52 pm

    I have a pair of smooth leather chukkas similar to the Ralph Lauren pair you posted. Can you dress these down with dark denim and a button down? Or is that too far? I’m new to the chukka game. Thanks in advance!

    • Reply
      November 11, 2015 at 4:02 pm

      Absolutely! I would recommend denim with a tapered leg (sleek shoes look goofy with baggy leg openings) and try cuffing them to break up the lines a little. If it still looks too casual, throw on a sweater over the button down to elevate the overall look.

  • Reply
    November 12, 2015 at 6:53 am

    Hey Nate, new to the website, found you from B&D. Im hooked! In college going to study abroad in London this winter. Will these boots hold up to the London rain? Thanks, looking forward to more good stuff.

    • Reply
      November 12, 2015 at 11:44 am

      Not the Clarks desert boots. They become extremely slippery in rain. A sewer cover just may be the end of you in these boots. But there are other brands out there that offer better traction and weather protection. Check out the Allen Edmonds Dundee. They should do the trick.

  • Reply
    March 14, 2016 at 1:21 pm

    I have the exact boots you have in the pics. Took some getting used to as far as the fit goes (feels like you’re going to step right out of them but I have found I can run in them if I need to move quickly).

    I usually pair them with chinos (from regular khaki to garment dyed in a variety of colors). I don’t yet own a pair of “nice” or “dressy” jeans but I can imagine they’ll look sharp when paired with them.

    • Reply
      March 14, 2016 at 6:47 pm

      That’s exactly how I felt. I must’ve walked back and forth in my house for an hour trying to decide if I was going to keep them, haha. But now, they’re some of my favorite shoes. They look fantastic with raw denim. Let me know if you need any suggestions.

  • Reply
    September 3, 2016 at 4:04 pm

    Great article, just ordered a Beeswax pair. Those photos looked weird to me for a while, until I realized why: you don’t have your beard, haha! Almost didn’t recognize you.

  • Reply
    October 15, 2016 at 10:00 pm

    Nate: I’m looking for a dress boot alternative to a hiking boot. Will the chukka have enough support to prevent pronation ? I have very flat feet and the ankle hiking boot design has been my go to thus far.

    • Reply
      October 19, 2016 at 5:15 pm

      Most desert boots, Clarks included, have nearly zero ankle support and flat insoles with little to no arch support. You might have to stick with the hikers.

  • Reply
    Daniel Adam
    December 4, 2016 at 9:28 pm

    Do you use any care products for its leather? Or the beeswax version is already oiled and the leather will not dry out any soon?
    I’ve just ordered mines through Amazon and I hope I will love them as you!
    I want to pair them with raw denim and chinos.

    • Reply
      December 6, 2016 at 4:38 pm

      I treated them once about 4 years ago with a homemade beeswax based leather balm but I actually wish I hadn’t because it darkened them a bit. They should be fine for years and years with no treatment.

  • Reply
    December 13, 2016 at 12:57 am

    Hey I’m looking into buying some Clarks, but I live in South Florida and it rains more than people think down here. Will the desert boot hold up to some decent rain? What would be better suede or leather? New to the boot game, just looking for advice.

    • Reply
      December 14, 2016 at 2:25 pm

      Clarks desert boots don’t do very well in the rain. The crepe soles become very slick on metal surfaces like stairs and drain covers and the leather soaks up water like a sponge. I would keep looking if you need something to handle a lot of rain.

  • Reply
    June 9, 2017 at 4:13 pm

    Clarks are awesome, their suede chukka boots are spectacular

  • Reply
    October 3, 2017 at 12:50 am

    Finally bit the bullet and bought these. Bushacre 2’s in dark brown. I bought them 1/2 a size smaller and they fit perfectly and I have medium to high arches. Thanks for the recommendation and the outfits you pair them with!

  • Reply
    November 29, 2017 at 3:08 am

    Hi, where did you get the cotton trousers from?

  • Reply
    November 29, 2017 at 7:23 am

    Great article. I’m looking for a decent pair of chukkas for work (in an office) as well as my commute and going out from time to time in Chicago. I like the Clark’s original & Bushacre 2’s, but can’t decide which to get.

    While the Bushacre is about 40% less expensive, would you still recommend the Original over them? If so, why?

    Also, it’s is Chicago…so the weather ranges quite a bit. I see above you don’t recommend th Clark’s for rainy environments, but I also don’t really want to drop $250+ on a pair.

    What would you recommend here?

    Thanks in advance

    • Reply
      December 12, 2017 at 9:37 am

      Definitely go for the original over the Bushacre. The crepe soles on the original look and feel much more authentic. For mixed weather, I’ve had the best luck with boots from Dr. Martens. They have plenty of traction in the wet and sloppy streets and are very water resistant. Also, they’re affordable enough that I won’t cry if they get trashed.

  • Reply
    Marion Pointer
    December 2, 2017 at 3:26 pm

    Wore chukka boots all through the 70s and they were the most comfortable shoe for walking, as walking was more common than driving in Europe back then.

    I am now in my 60s and have purchased a pair as my husband and I have started to tour the various states. No problems with this old lady’s feet and I intend to keep them that way.

  • Leave a Reply

    About Me

    Casual Style 101

    Free style guide