How to Style And Wear Men’s Chukka Boots

How to Style And Wear Men’s Chukka Boots

Chukka boots are an essential part of any man’s wardrobe. Their simple, timeless style makes them easily adaptable to any outfit, and they also provide comfort and support throughout the day. Whether you’re looking to create a smart-casual look or something more rugged and outdoorsy, chukka boots are the perfect choice. In this guide, we’ll show you how to style and wear men’s chukka boots for any occasion.

Every man needs at least a pair of Chukka boots in their closet. They are classy, fashionable, and stylish all at once. The best thing about Chukkas, though, is the fact that they can be very versatile, pairing well with both casual and formal outfits.  

We’ll take a look at everything you need to know about styling Chukka boots and help you cut an effortless style that’s chic and on-trend. Learn how to style Chukkas for different seasons and different occasions, and also arm yourself with the knowledge of what mistakes to definitely avoid when styling Chukka boots.

Let’s take a look at what makes these interesting sounding boots such a great addition to your wardrobe.

What are Men’s Chukka boots?

How to Style and Wear Men’s Chukka Boots

Image credit: rebelsmarket 

While we’ve already stated that a pair (or two) of decent quality men’s Chukka boots is a must-have wardrobe staple for any guy - you might be wondering; what even are Chukka boots? With such an unusual sounding name, you’d be forgiven for being curious.

Chukka boots are a timeless type of shoe that get their name from chukka, a period in the game of polo. They became popular in 1924 thanks to the Duke of Windsor wearing them. 

Chukkas are sometimes knee-length, typically featuring thin laces and two or three grommets, but modern styles have seen them shrink down to be ankle-length boots. Most of them come in brown hues and are made of either suede or leather - but you can, of course, find edgy and unusual styles out here too.

Interestingly, there’s no real clear cut answer to where Chukka boots got their interesting name. Perhaps the most readily accepted theory is the one that suggests the name ‘Chukka’ comes from the game of Polo. In this game, a Chukker or Chukka is the term given to the seven and a half minute playing period - and comes from the Hindi word for circle (chukkar). 

It’s thought that the nickname ‘Chukka boots’ was given to this type of boot because of their slight resemblance to the jodhpur boots worn by polo players. The more you know, eh? 

How to Style Chukka Boots for Men

How to Style and Wear Men’s Chukka Boots

Image credit: rebelsmarket 

If the story about how Chukka boots allegedly got their name tells us anything, it’s that they are at once characteristically casual, sporty, and also smart - making them a diverse and versatile piece of men’s footwear suitable for lots of different occasions. 

A firm favorite for relaxed ‘outdoorsy’ looks, Chukka boots can also be worn as dress shoes to complement smart casual or business casual outfits. 

Let’s take a look at different ways to wear men’s Chukka boots, how to style them, and what to wear with them:


Warm weather casual look

How to Style and Wear Men’s Chukka Boots

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With chukka boots, it’s perfectly easy to pull off a breezy, ‘outdoors’ casual look. The boots are smart enough to make an outfit look put together, but also have a sports-style influence that usually goes very well with jeans and basic men’s cotton t-shirts or light springtime jackets. 

Consequently, you can style Chukka boots with warm weather outfits easily. Wear a crew-neck shirt with a pair of black jeans, then complete the look with some suede Chukkas. Keep the boots simple, though. While you can get your hands on Chukka boots with visible stitching and contrasting materials and paneling - we recommend going for a pair with block color and a single texture throughout. This ‘dressed down but dressed up’ look is perfect for warm weather daytime wear. 

Also, feel free to lean into the sporting aspect of this style. You could also wear Chukka boots with an oxford shirt or polo shirt and jeans for a fun, easy-going look. 

Warm weather dressed-up look

How to Style and Wear Men’s Chukka Boots

Image credit: lookbook 

Leather Chukkas are perfect for a semi-formal dressed-up look. It goes without saying that genuine leather is a great option, but you can also style a dressed-up look with imitation leather Chukka boots.  Pair these with a dark denim button-down shirt and corduroy trousers (or dark jeans)  and you’re good to go. 

Keep in mind that darker shades of Chukkas look more formal than lighter ones. It is up to you to decide where you want to fall on the spectrum. A few carefully placed pieces of jewelry or accessories can help to complete the look; add a silver or gunmetal watch on your wrist and a pair of cufflinks, or keep it chic with just a leather belt to tie everything together. 

Cold weather casual look

How to Style and Wear Men’s Chukka Boots

Image credit: lookastic 

Chilly weather is best suited for wearing something casual like a Henley-style shirt, with its masculine look. Combine this with a leather jacket and a pair of Chukka boots. For the cold, a Henley-style top with thermal insulation is exactly what you need as a stylish and casual base layer that you can layer up with jackets and shirts to keep warm.

The Henley’s band collar and durable look give the entire outfit a rugged look. It is a lot more casual than a plain and simple long-sleeved t-shirt and plays off the sporty aspect of Chukkas perfectly. 

Cold weather dressed-up look

How to Style and Wear Men’s Chukka Boots

Image credit: lookbook 

A great look to go for when it gets chilly out is chukka boots worn with a pair of dark pants or jeans, a patterned shirt, a V-neck sweater for the cold, and some dotted socks. Bolder colors like maroon and navy blue for the sweater will also look great in this kind of weather.

Alternatively, you can up your layering game, and pair Chukka boots with a winter jacket and a woolen sweater with a collared shirt underneath. Just keep the color palette dark for this one as it’s a dressed-up look for the evenings. 

Do’s and Don’ts of Styling and Wearing Chukka Boots

How to Style and Wear Men’s Chukka Boots

Image credit: rebelsmarket 

As with most men’s boot styles, there are of course certain dos and don’ts. Even the most rebellious fashion style has to follow certain rules to look stylish- so we’ve put together a quick and dirty guide to what you should (and most definitely should not) do when choosing, wearing, and maintaining your Chukka boots:


  • Clean your Chukkas regularly

  • Use a suede protector and nail brush to brush off marks and remove dust off the boots

  • Be careful about the length of your trouser. The hem of trousers should just graze the top of your Chukkas


  • Don’t opt for leather soles, choose rubber ones if possible. Leather soles squeak and can be rather slippery

  • Don’t wear loose or long formal trousers with Chukkas (this will make you look dated and cut an odd silhouette) Stick to chinos, corduroys, and jeans.

  • Don’t use the wrong cleaning products on your Chukka boots. While leather needs polish and moisturizer - you should never use these to clean suede. They’ll ruin your shoes

Add Chukka Boots to Your Capsule wardrobe

As you can see, men’s Chukka boots can be very versatile. Depending on what is in your closet, you can make these shoes your go-to pair of footwear and no one will question your sense of style.

 The idea here is to simply play around with what you have and just get a little creative. And if you do not own a pair of Chukkas, it’s time to head out and get some! 

You might also want to look at:

The Biggest Mistakes Men Make When Styling Skinny Jeans
What shoes to Wear With Different Cuts Of Jeans For Men
What to Look For When Buying Jeans For Your Body type 
How to Shop For Custom Leather Shoes 


About the Author

Riley Davis

Writing allows me to express my creative thought process through words. I hope you enjoy my style! Go Rebels!