Style 101: How to Wear Chukka Boots

August 7, 2020
Classic Chukka Style: East Dane showcases how to wear chukka boots. The men's retailer pairs Rag & Bone chukka boots style with the iconic look of Baracuta's G9 Harrington jacket.
Classic Chukka Style: East Dane showcases how to wear chukka boots. The men’s retailer pairs Rag & Bone chukka boots style with the iconic look of Baracuta’s G9 Harrington jacket.

How to wear chukka boots should be part of your style repertoire. The chukka boot is classic footwear that offers a lot of versatility, along with a broad and timeless appeal. You can go from casual to smart by just putting on a different pair of pants. Its popularity took off in the late 1940s and 1950s as a sophisticated variant for casual wear. One of the unique aspects of its design is that this ankle-length boot comes with three pieces of leather and two or three eyelets which differentiate it from other types of footwear. As far as materials are concerned, either calfskin leather or suede is prevalent.

Related: The Boot Edit | Timeless Boot Styles

Chukka boots are also known as desert boots. The comfortable essential suits many styles. Here, model Jeremy Young wears a pair of Vince suede chukka boots from East Dane.
Go Professional: Chukka sneakers are a great way to revisit the classic. A little dressier than the average sneaker, they wear well with relaxed tailoring. Pictured above, model Jake Davies sports Vince Camuto chukka sneakers with more fashions from the brand. You can also find more traditional fashions on websites similar to Adoniya.

The History of Chukka Boots

The name of these boots originated in colonial India and came from the sport of polo where chukka is a period of play (7 minutes long). British army units used to wear it while playing the “Sports of Kings.” It was famously worn by the Duke of Windsor in 1924, after which it exploded in popularity amongst the British army. The exact origin of these boots remains unclear, but its classic appeal made it so famous that it found its way to the West.

Timeless Chukkas: All smiles, Christian Slater connects with Mr Porter. Embracing laid-back style, he sports suede Marséll chukka boots.
Timeless Chukkas: All smiles, Christian Slater connects with Mr Porter. Embracing laid-back style, he sports suede Marséll chukka boots.

What Are Chukka Boots Made Out of?

Chukka boots are traditionally made out of either leather or suede. Let’s take a look at what makes them unique:

  1. Leather Chukka Boots: They are more durable than suede and will show less wear over time, which adds to its value. Leather also ages exceptionally well and gives off a classic and rugged look and feel over time.
  2. Suede Chukka Boots: These are very comfortable to wear and are ideal for smart casual and business casual occasions. You do have to take extra care of them to ensure that they last long without too much wear.
Wearing UGG Neumel Twinface Chukka boots, KYLE stops by the last phone booth in New York City.
Street Chukka: Wearing UGG Neumel Twinface chukka boots, KYLE stops by the last phone booth in New York City.

How to Wear Chukka Boots: Style Guide

If you are interested in knowing how to wear chukka boots, you’re at the right place. These iconic boots have become a favorite for both the masses and celebrities alike. Even designers wear them, which is a testament to how versatile it is. No longer do you have to be stuck in a rut when it comes to fashion. All you have to do is slip on a pair of jeans and put on your chukka boots to make a fashion statement instantly.

Relaxing at a diner, Daniel Bamdad sports a bleached jacket with distressed jeans and chukka boots from boohooMAN.
Contemporary Cool: BoohooMAN stands by the chukka boot. While the retailer is known for its trendy styles, no one can say no the classic qualities of the chukka boot. Here, you can see it with a bleached denim jacket and distressed jeans.

If you don’t feel like wearing casual wear, then just put on your favorite blazer and chinos. You will still look amazing in those boots. Whether you are wearing skinny jeans, sweaters, blazers, or even a coat, chukka boots pairs exceptionally well with most outfits. The best types of socks to wear with these boots are no-show or ankle-length. If you have ever wondered “how to wear chukka boots?” then here are a few ideas:

  1. Casual: Chukka boots are inherently casual in their design. Wearing them with pretty much any color of jeans gives a casual yet classic look. It goes exceptionally well with shirts and denim jeans as well.
  2. Smart Casual – For a stylish casual look, you may wear dark-colored chukka boots and pair them with black jeans, a T-shirt and a blazer. If jeans aren’t your style, you can wear chinos instead, and it still will look amazing.
  3. Business Casual – If business casual is what you prefer, then all you have to do is pair your chukka boots with a shirt, cashmere sweater, blazer, and a pair of trousers.
Bjorn Iooss photographs Justin Theroux in a Saint Laurent buffalo check shirt with Gucci jeans and a t-shirt by The Elder Statesman. Theroux also sports Marséll washed-suede chukka boots.
How to Wear Chukka Boots with Jeans: One easy way to pull off chukka boots is to pair them with denim jeans. Here, Justin Theroux sports a Saint Laurent buffalo check shirt with Gucci jeans and a t-shirt by The Elder Statesman. Theroux also wears Marséll washed-suede chukka boots.

What Are Some of the Best Chukka Boot Brands Today?

There are plenty of brands in the market but the below five are amongst the most reliable and popular ones today:

  • Clarks: This brand is for all the purists out there and is well known for making very high-quality chukka boots. If you want to buy authentic chukka boots, this is the place to check out.
  • Hudson: They provide a wide selection of high-quality chukka boots at affordable prices and multiple color options, making them very popular amongst young adults.
  • Grenson: Grenson has been known for making excellent classic style chukka boots since the 1930s and has never wavered when it comes to quality craftsmanship.
  • John Lewis: Another great affordable brand, John Lewis, provides excellent value options fit for smart casual and formal occasions alike.
  • Cheaney: They are one of the most respected British Shoemakers who have been handcrafting Chukka boots for more than a century. They are very well known for their boots which come with a fur lining and extremely high-quality craftsmanship.
Style 101: How to Wear Chukka Boots
Weekend Dress-Down Style: Don’t be afraid to mix brown chukka boots with dark colors. Here, model Claudio Monteiro inspires in quite the outfit. J.Crew pairs its suit jacket with a chambray shirt, denim jeans, and chukka boots. The essential items come together for one sleek look.
Reading, Jeremy Young sports a Vince reversible sherpa hooded vest $325, double layer sweater $325, jeans $195, and suede Chukkas $350.
Everyday Essential: Chukka boots are also known as desert boots. The comfortable essential suits many styles. Here, model Jeremy Young wears a pair of Vince suede chukka boots from East Dane.
Malik Lindo embraces smart style with a bomber jacket, polo, and trousers by Ted Baker. Malik's look is complete with a pair of John Varvatos Star USA Chukka boots.
Leather Chukka Boots: Looking to elevate your style with a pair of chukka boots? Look no further than a style in leather. Model Malik Lindo embraces smart style with a bomber jacket, polo, and trousers by Ted Baker. Malik’s look is complete with a pair of John Varvatos Star USA Chukka boots.
UGG caters to our need for comfort with its lined chukka boots. They look great with a pair of joggers or jeans. RJ King goes casual in a pair of UGG Neumel chukka boots.
Casual Ease: UGG caters to our need for comfort with its lined chukka boots. They look great with a pair of joggers or jeans. RJ King goes casual in UGG Neumel chukka boots.
Starring in H.E. by Mango's advertising campaign, Spanish model Andres Velencoso Segura shows a great way to pull off suede chukka boots. The essential boots complement dark washed denim. They also go great with a smart shirt and jacket combination.
Smart Style: Starring in H.E. by Mango’s advertising campaign, Spanish model Andres Velencoso Segura shows a great way to pull off suede chukka boots. The essential boots complement dark washed denim. They also go great with a smart shirt and jacket combination.

Shop Men’s Chukka Boots

ECCO Melbourne Chukka Boot
ECCO Melbourne Chukka Boot
Embrace a sleek everyday look with this leather chukka boot from ECCO.
Rodd and Gunn Pebbly Hill Chukka Boot
Rodd & Gunn Pebbly Hill Chukka Boot
Tap into a classic style with these suede chukka boots from Rodd & Gunn.
UGG Neumel Chukka Boot
UGG Neumel Chukka Boot
Comfort and style are instantly yours with UGG’s UGGpure-lined chukka boot.
No posts found.