The Ultimate Guide to Men’s Chukka Boots


Wondering what type of boots you should invest in this season? Here at The Idle Man we like to give our readers the best selection and styling advice possible. Thanks to this quick and easy guide you’ll find everything you need to get yourself a top pair of Chukka boots.

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It’s extremely important for every man out there to have a varied selection of shoes to choose from. Footwear has the power to make or break an outfit and today we’ll focus on a menswear classic: Chukka boots. After this guide you’ll definitely find the right pair for you. As always, we’ll throw in some styling ideas to give you a bit of inspiration for your outfits.

What are Chukka Boots?

We couldn’t possibly start without answering this fundamental question that no one seems to have the answer to. Fear not, we can solve the mystery. More often than not, when talking about Chukka boots, people have desert boots in mind. And they’re not entirely wrong.

In fact, all desert boots can be classified as Chukkas. However, just when you’re starting to think that there’s no difference between the two, it gets a bit trickier. And that brings us to a deeper examination of these boots’ shape.

brown desert boots for men
Desert boots and chukka boots are not entirely different, so don’t worry if you get them confused


Chukka Style

Unfortunately, the desert boots street doesn’t go both ways. Not all Chukkas can be described as desert boots. As a matter of fact, desert boots are a specific kind of Chukka boots – that’s why all of them can be included in this broader category. These boots owe their name to polo matches, with chukka being a period in this sport.

It’s more likely that their association to polo is due to players wearing them after rather than during matches. However, they became extremely popular after the Duke of Windsor wore them in 1924 on occasion of a visit to the U.S. After that these boots steadily continued to gain a large number of fans throughout the 40s and 60s.

chukka boots for men streets style
Chukka boots became popular in the 1940s after the Second World War


These boots usually feature two or three eyeholes, leather soles and thin laces and can be more generally described as ankle boots because of their height. The quintessentially Chukkas traditionally come in dark brown. However, you can find them in a broad range of different leathers, usually suede or calf.

Best Chukka Boots for Men

Now that we’ve shed some light on what makes a Chukka boot, it’s time to have a look at some of the best pairs available to you. Whether you prefer a more classic pair or you’re all about functionality, we have different options for you to choose from.

Hudson Chukka Boots

If you’re looking to get your hands on the real deal, with a pair of Hudson Chukkas, you’ll have the most iconic and durable boots without breaking the bank. Made from strong, natural leather and featuring a multi-layered sole, these boots are a safe investment that will surely pay off for years to come. Choose from either a leather pair or opt for the suede options.

black hudson chukka boots for men
Make sure that your chukka boots are durable enough to last you a few years


Red Wing Chukka Boots

Just in case you’re going for a more premium feel, these Red Wing boots, are right up your street. Thanks to a contemporary design that still deeply references the practical needs of true outdoorsmen, these Chukka boots are the perfect mix of technical footwear with a stylish and heritage feel.

red wing boots for men
Red Wing boots are perfect for both a night out and that big work meeting


Comfortable Chukka Boots

Even though Chukkas are a smarter option as opposed to desert boots, it doesn’t mean that they can’t be comfortable. With their subtle stitching and smooth surface, you have an elegant yet easily wearable pair of boots. However, if you’re more interested in owning an ultra comfortable and good quality pair of Chukka boots, Timberland boots are just what you need. With their relaxed look and smooth fit, you’ll be able to easily work them into any outfit.

timberland chukka boots for men
Accompany your blue suede chukka boots with some smart chinos and you’re ready to hit the town


Suede Chukka Boots

The most important thing about suede shoes is knowing how to properly care for them so you can wear them for as long as possible. Caring for your suede shoes is easier than you may think as you can buy shoe protector spray that can easily be sprayed over your new suede shoes. As well as protecting the suede shoes, the same can be done for your leather chukka boots as you will want to keep the material hydrated and looking fresh.

Chukka boots should be looked after so they can look newer for longer


 Best Desert Boots for Men

Since they’re also part of the family, it’s worth having a look at some quality men’s desert boots. Starting off as a top favourite amongst WWII soldiers, these boots were mainly introduced to the commercial masses by Clarks in 1949. Clarks dessert boots always feature crepe rubber soles, double eyelet and thicker laces, desert boots have successfully transitioned from the African desert campaigns led by the British army to the feet of men all across the globe.

Black desert boots are without a doubt the most versatile ones out there. You’ll be able to dress them up with suit trousers or down by simply wearing a pair of jeans.

Dress your chukka boots down with a nice blazer and t-shirt
PHOTO CREDIT: Christoph Schaller


How to Wear Chukka Boots

For a smart casual take on your Chukkas, you can pair them with a denim shirt and slim chinos. These outfit also allows you to play around with some layering combinations so that you can fight off the cold temperatures in style. You can even go as far as Zac Efron who takes it to the next level by wearing a thin quilted bomber jacket as well as an overcoat.

zac efron brown chukka boots mens street style
Zac Efron’s affiliation to the chukka boot has gained quite the notoriety in the fashion world
PHOTO CREDIT: The Fashionisto


Ultimate Guide on The Best Chukka Boots

  • All desert boots are Chukkas but not all Chukkas are desert boots – hard to grasp but once you’ve got it, you will be an expert in no time.
  • The key features of the boot are two or three eyeholes, leather soles, calf or suede uppers, thin laces and are ankle-high.
  • There are many Chukka boots on the market, Clarks being the originals that started off the entire trend.
  • Styling the Chukka boot is easy – smart casual autumn/winter layering essentials: a quilted jacket, denim shirt, smart trousers and of course, the Chukka boots.
clarks desert boots mens street style
Don’t be afraid to wear your chukka boots for whatever the occasion
PHOTO CREDIT: He Spoke Style

On That Note

It’s safe to say that Chukka boots are an absolute staple piece in men’s footwear. And now with the different options and brands for you to choose from, getting right pair for your personal sense of style and fashion needs will be a piece of cake. Whether you’re planning on taking them for a walk in the woods or to the pub for a drink, these boots are an extremely versatile seasonal must.


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