The Quintessential Guide to Chukka Boots for Men

‘Looking good is good business’Anonymous

Chukka boots or Chukkas are a comfortable, stylish pair of shoes that every gentleman should own in his closet.

If you’re looking for a shoe that exudes confidence, class, and style 

but is also elegant and playful, then a pair of Chukkas is the perfect shoes for you! Chukkas are extremely versatile shoes that can fit many different outfits, effortlessly!

Want to know more about Chukkas? Like how to wear them and style them so you come out looking awesome? Keep reading to find out more about these awesome shoes.

What are Chukkas?

Chukkas are ankle high boots usually made of leather or suede with the soles made of either leather or rubber. They come in various colors and styles. For example, you could get a pair that is open laced with two or three pairs of eyelets and a strap, or opt for a buckle if you prefer.

Did you know? Chukka boots were originally worn as military boots in South Africa and Britain. It was worn by soldiers in Britain’s infantry and later became known as desert boots.

After originating in the early 1900’s they’re now more famous than they were, it’s become clear that they’re a pair of shoes that have come to stay.

How to wear a pair of Chukkas

Chukkas are shoes that a gentleman can style effortlessly with many different outfits. The easy-going comfortable style makes it easy to pair with various fabrics and colors.

One great thing about these shoes is that it doesn’t matter your age – whether you’re a young or middle-aged man. There’s a pair of chukka boots for men of all ages!

Here are some tips for pulling off a fabulous look with your pair of Chukkas:

  • The Formal look

This is perfect for formal settings like meetings, formal dinners, or a wedding where you need to come through looking smooth and dapper.

You could wear a nice three-piece suit with a polka-dotted shirt, fitted trousers and a matching color of Chukka boots. Jeans are not formal attire so avoid them when trying to pull off the classic formal look. Dark-colored Chukka boots are preferable for formal occasions.

  • The Business Casual (Semi-formal) Look

This can be pulled off in a number of ways, either by donning a cool Blazer, a T-shirt, or wearing a dress shirt and letting it loose by not tucking it in. You can wear jeans or chinos to finish off this particular look, or simply roll up your dress shirt sleeves, donning your favorite chukka boots and you’re good to go. Light or contrasting colors like brown or beige are perfect for making a statement with your shoes!

  • The Casual Look                                                                                                                                                         

For the casual look, you can be as expressive as you wish! It also depends on the occasion you’ll be wearing your shoes. Are you going for a night out in town? A tour of the city? Or even a lunch date? You could wear a plain T-shirt and a pair of jeans with your favorite Chukkas and look super! The casual look is pretty easy to achieve. If you would like to dress it up a bit, you can wear a nice jacket to make your outfit a little more interesting, and you’ll still come out looking great!

Click here to design your own unique look 

Choosing the right pair

A few factors to consider when choosing a pair of Chukkas boots:

  • Size & Fit

Knowing your size is an essential part of choosing any type of shoe. When choosing a pair of Chukkas, select a pair that is neither too tight nor loose. The shoes should be a snug fit around your foot and have a sturdy sole.

The arch of your foot is also an important factor when picking a shoe and it depends on your foot type. You can have either a:

  • High arch
  • Normal arch or
  • Low arch (Flat foot)

If you’re flat-footed, consider getting a customized pair. You can never go wrong with shoes tailored to the exact dimensions of your feet.

  • Brand

Buying from the right brand is quite important, as it helps you to get the best value for your investment. Always buy your Chukkas from authentic sources. Having a trusted brand as your go-to will ease the stress of having to shop for new products and ensure good quality.

  • Color

Everyone has their unique preferences when it comes to colors. Whichever colors you fancy, there’s always a pair of Chukkas boots for you. However, if you’re on a limited budget, it’s a great idea to buy colors that match with most of the items in your closet. For formal occasions, dark-colored Chukkas boots are the usual go to because of their ability to seamlessly fit with any outfit. Grey, black and brown are the most common colors out there that you can pair with almost anything.

If, however, you’re simply looking to have fun, and you’ve got a solid budget in place, then why restrict yourself? Choose from a range of colors available and rock them like a star!


The material used in making your Chukkas can vary from suede to leather, what you need to do is ensure it’s the best material whichever material you prefer.

If you decide to get a pre-designed pair of Chukkas boots, feel free to choose your own material, one that you’re comfortable with.

Quality of construction

The quality of construction is a huge factor that should determine whether you buy a pair of Chukkas or not! There are a lot of shoe brands out there and some are low-end shoes as well! Stick with a trusted brand to get the best value for your money.

Here are a few tips on what to look out for:

  • A flexible yet durable sole that doesn’t crack when it’s bent in either direction.
  • The consistency of the material – Look out for discoloration in the material, does it fade around certain areas?
  • The inner sole finishing – You don’t want a pair of shoes with threads running loose at every end.
  • The condition of the laces – do they show signs of unraveling?

Keep this checklist in mind when searching for a pair of Chukkas boots to help you differentiate between a low-end pair and a high-end pair.

Last Words

If you would like a pair Chukkas that fit like a glove, the best option is custom-made footwear that’s tailored to your tastes and design.

Find all you need in one place here.