22 Best Chukka Boots for Men in 2023

Whenever we have to go to a semi-important event, we have an important decision to make, and that is whether we are willing to actually go with a more formal look to show off your current social stature or you could just go with something more casual to seem as friendly as possible to those around you.

But what if we told you that you don’t actually need to choose between the two after all? What if we told you that in reality, you can actually wear the same pair of shoes to a wedding that you could wear while going out to the bar with your friends?

As utopian as that may sound, the truth is that there is a pair of shoes that you can always rely on and that pair is always going to be your finest chukka boots.

In case you have never heard of chukka boots before, it is a style of ankle boot that is very similar to a desert boot, with the main difference between the two being in their practicality.

While desert boots are a lot more niche as far as utility reasons go, chukka boots are way more universal in nature, as you can easily wear them all throughout the four seasons without a care in the world, even when it’s raining and you need waterproof boots.

So, in this guide we would like to provide you with a little intro as to what makes chukka boots so special and why you should invest into them, and then we’ll give you our unbiased list of the absolute best choices you could make today.

You don’t have to listen to us word for word, but give us the benefit of the doubt in that we don’t actually earn anything by giving you wrong choices, this is just what we personally believe to be the right picks, alongside all of the millions of other satisfied customers that have tried them on for themselves and gave us their opinions.

With that said, let’s properly start off this guide by answering the following questions:

What Makes Chukka Boots Special?

We mentioned previously how chukka boots are actually very similar to desert boots in both looks and feel, although the main difference between the two is always going to be the fact that desert boots have a crepe sole while chukkas very rarely ever have one.

On top of that, desert boots uppers are always suede, while chukka uppers can also be suede, but they can also be calfskin or basically any other synthetic material whatsoever.

Another notable contender for the chukka boot rivalry is the Chelsea boot. These are also ankle boots which is why many people mistake them for one another, but you can always spot Chelsea boots by their lack of laces and specifically those bands of elastic that they have around the top to make them fit you better.

What to Look for in Chukka Boots?

There are quite a handful of different requirements that you should tick off when shopping for a good pair of chukka boots for yourself.

Price

First and foremost, you need to keep into consideration your budget. There are currently three different subcategories that go into this box and they are the following:

• Budget options – typically around $50-$100 although that may vary depending on your other choices.
• Mid-Level – these usually range between $100-$200 and they come in different colors and you can sometimes pick between different materials and such.
• Grail – this is by far the most expensive option and they range between $200-$400, with a few exceptions costing even more than that depending on how niche and personalized you want your boots to be.

Color

Secondly, you can also separate different chukka boots based on their color. For example, we have black chukkas which are amongst the most popular choices when it comes to making that formal outfit really shine.

Dark brown chukkas on the other hand is a much more versatile choice simply because you can match it with a lot wider of a range of fits.

The Tan/sand chukkas are also very popular and they go very well with a lot of different costumes they go with, and let’s not forget about the gray chukkas which are pretty much famous for casual fits.

Blue chukkas are also very popular despite being a bit more of a niche design choice. Suede is the most common choice for these chukkas and they can really compliment your look a lot.

Sure, there are a ton of other chukka color schemes that you could go for, but these are the most popular ones out there. You can really stand out with a pair of black chukkas, but for the most part you will should stick to the basics unless you’re sure of your choice.

With all of that out of the way however, we should delve into our top 22 already, starting off with:

22. Oak Street Bootmakers Trench Chukka

This brand has pretty much already made it known that when it comes to the quality of its chukkas, it will not settle for anything but perfection, and this truly shows especially with their Trench model.

21. Rhodes Tyler Chukka

Rhodes’ roughout model is one of this generation’s best and that says a lot considering just how many incredible models have hit the scene as of late.

If you’re looking for a more affordable and yet still very slick model then this may actually be a match made in heaven for you.

20. J. Crew MacAlister Boots

If you’re on the market looking for a pair of luxurious chukkas then J. Crew have got your back because while these may look a bit rugged at first sight, they will only get better with age, showcasing the fact that Father Time doesn’t take its toll on everything equally.

All jokes aside, this is a classic model that you can’t go wrong with, so why not invest in this pair? You won’t regret it, trust us.

19. Taylor Stitch Unlined Chukka

A lot of famous pairs of chukkas came directly from Leon, Mexico, and this one’s no different.

It is an all-season-ready pair that looks like a million bucks and feels about as comfy as you can expect from the foam insole that it comes with.

18. Viberg Bernhard Boot

While we usually wouldn’t recommend going this far outside of your budget range, there’s just something so absolutely stunning about these boots that we just can’t get enough of.

Is it the overall quality that they boast with? The vintage design? Or is it everything under the sun? Honestly, we can’t decide, so we’ll just go for the latter for now.

17. Frye William Monk Chukka

The coolest part about this design is in its name. That’s right, this pair of chukka boots comes with a monk strap which makes it easy for you to slip in and out of them.

On top of that, despite not being the most affordable model on the market, we would argue that it is one of the most comfortable ones since it is made to be worn around for many hours every day of the week.

16. Yuketen Maine Suede Derby Shoes

We can’t get enough of these handsewn chukkas right here and that is simply because of how unique each and every model is.

As we mentioned previously, they are all a hundred percent handsewn, meaning that no matter who you are or how much you spent for it, your pair of Yuketen chukkas are unique on this planet which is definitely something that we could all make use of nowadays.

15. Rhodes Dylan

Rhodes Dylan is one of our personal favorites, but it’s not for the reasons you may think.

If you’re a fan of the stylish sand shoe design you will absolutely love it, but all that aside, the quality Italian leather really shines here, making these some of the smoothest and most comfortable shoes you could wear.

14. Clarks Desert Boot

Let’s just say that if you’ve gone to a handful of official events in your life then chances are that you already know all about these boots right here.

The truth of the matter is that Clarks offer you some of the absolute best footwear we could think of, and what makes them all the better is the fact that they’re made using premium oak nubuck leather which is just the icing on the cake for these beauties.

13. Lems Boulder

Despite the fact that the Lems Boulder look nothing like the traditional chukkas that we’ve come to expect from the fashion world, the truth is that they fit all the brackets to count as one so who are we to judge?

And on top of that, if you actually like the stranger design you will be rewarded with the otherworldly comfiness that these boots have to offer which is definitely a plus in our book.

12. Cole Haan Colton

If you’re looking for the very best pair of chukkas to wear around winter time then look no further than the Cole Haan Colton because these are some of the absolute best boots on the market for that.

We’re talking about a 100% premium leather upper and of course, the unique traditional design of the cross-lace which you just can’t go wrong with.

11. Thursday Boot Co. Scout

Thursday Boot Co. have pretty much established themselves as the creators of some of the most iconic men’s boots of all time.

Regardless of whether you love their older styles or if you’re more inclined to gravitate towards their newer looks, you will always find a good model to choose from amongst their lineup and the Scout is by far one of our personal favorites.

10. Nisolo Emilio Chukka Boots

But hey, sometimes you don’t want something modern at all, sometimes you want to go with the classic and that’s fine. At the end of the day, there’s a reason as to why these classics were able to withstand the test of time and that’s all based around the overall quality they have to offer.

This is why we wholeheartedly recommend that you get yourself a pair of these Peru-made models that were handcrafted by the literal best craftsmen in the country.

9. Tod’s UK Leather Desert

We should mention here as a little disclaimer that if we were to talk about quality alone then this pair would definitely be at the top of the food chain simply because it is unmatched as far as its build goes.

But, and this is a very big but, the real kicker to the nards here is the price tag as you will often times struggle to find one online that goes for less than $600. If you can handle that price tag, definitely go for it, but if not then you have plenty of other models to choose from on our list.

8. Allen Edmonds Williamsburg

Allen Edmonds is one of those designers that comes only once-in-a-generation and that’s a fact. Most gentlemen out there would kill to be able to own one of these and we can completely understand where they’re coming from.

The premium calfskin leather, the single oak leather sole and the 360-degree Bench Welt is enough to turn anyone into a fan, and trust us when we tell you that you will absolutely love the attention you will get when you walk up to a crowd wearing these.

7. Mark McNairy D-Ring

In case you haven’t heard of Mark McNairy before don’t worry, you’re not the first. This just means that you haven’t been keeping up with the more contemporary designers of our generation, which is again, very understandable.

Even so we urge you to check out this model and if you like what you see we always recommend that you check out the designer’s other work as well because Mark McNairy is not one to disappoint.

6. George Cleverley Nathan Distressed

This pair of chukkas is very iconic to say the least, as it is meant to perfectly portray the gentleman of the past in all of his glory.

Did they succeed? Definitely let us know by either purchasing one for yourself for your next big event.

5. Rancourt Blake

The chukka that Rancourt Blake has to offer is yet another perfect example of a classic design making its way into the 21^st century.

Despite having a ton of different modern additions to its traits and components, it still keeps that traditional look that we just can’t get enough of.

4. Red Wing Heritage Weekender

This is one of the most popular brands of men’s footwear that we could think of, to the point where it’s extremely hard to even picture the industry without their most notable contributions.

Despite being around for over 100 years now, we would argue that their Weekender chukka is still the absolute best model they ever released to the general populace and if you think otherwise, we would seriously like to question your devotion to the history of the industry to say the least.

3. Frye Bowery

Frye is by far one of the most famous men’s footwear brands out there, and that is very much so thanks to their high-end dress models.

The Bowery chukka is a perfect example of this, as many have pointed out that the Bowery is the result of over 150 years of trial and error that they’ve amassed so far.

2. Lemaire Taupe Suede Desert

This is a very interesting pair of chukkas, and that is all due to their angular design choice and of course, that color shade.

The refined curvature and the rounded edges are also very good at complimenting the amount of work that was put into creating these beauties and honestly, even though we can’t put them above our number one pick, we would still love to recommend these to anyone that is currently on the lookout for a new pair of chukkas.

1. Quoddy Kennebec

Quoddy is by far one of the most respectable names in the industry and even if you have never tried one of their models before we wholeheartedly believe that they’re some of the best options out there.

Regardless of what your current budget is, you should always try to get yourself one of their pairs because they will last a lifetime, to say the least. And these Kennebec boots also look really cool, matching both casual and classy outfits.

Conclusion

With all of that being said, is there any actual way that you could list off every good pair of chukkas on the market? Absolutely not.

So, if your favorite pair or brand is not on here, we highly recommend that you make it your mission to wear it around everywhere and make it known that it is worth the investment to you.

But for now we would like to thank you for reading and we hope that you got something out of this whole guide. Stay safe out there and remember that you should never cut down on the quality just to save a few bucks, especially not when it comes to footwear.