The Best Chukka Boots Style Guide

How To Wear Chukka Boots Style

The Best Chukka Boots Guide Most Wearable Boot Style

No gent’s collection of shoes is complete without at least one pair of chukka boots. The classic footwear style is a staple for any closet and offers a unique aesthetic that other shoes cannot. Ideal for casual outfits yet easily dressed up for smart ensembles, these must-have boots are versatile and fashionable. So, if you don’t own a pair, it’s time to invest. Once you’ve found the right option, all you need to know is how to wear them for a sharp and stylish look. Luckily, we can help with that and show you how to wear chukka boots the right way.

What are Chukka Boots?

Chukka boots are a classic style of footwear. They are thought to have received their name from the game of polo, in which a chukka is a period, and became extremely popular after being worn by the Duke of Windsor in 1924. Chukka boots are ankle-length type of boot that typically features two or three eyelets and thin laces. They are often made from leather or suede and most commonly feature a brown hue.

Chukka Boots vs Desert Boots

Desert Boots vs Chukka Boots

Many gents are confused about the difference between chukka boots and desert boots, and it’s easy to see why. The two footwear styles appear incredibly similar and are closely linked. Desert boots are a particular type of chukka boot, which serves as a broader category of shoes. The main way to identify which is with the sole; Desert boots, which are based on the boots worn in desert campaigns by British soldiers, typically feature a crepe rubber sole. They also tend to be more casual in material and construction than other chukka boots.

How to Wear Chukka Boots

Although chukka boots are inherently casual, they can also be worn as dress shoes and suit both smart casual and business casual outfits. All you need is the perfect outfit to pair them with, which is where we can help.

Casual Occasions

Casual Occasions

Rocking your chukkas for a casual dressing look is easy. These cool boots are great shoes to wear with jeans and can match a range of tops and jackets. For an impressive ensemble, try pairing your boots with blue jeans, a white button-down, and a denim jacket. Just remember to select a relaxed style of chukka boots, such as a suede design in a brown hue, for the perfect finishing touch.

Smart Casual Occasions

Smart Casual Occasions

Due to their classic shape, chukkas can also make an excellent option for smart casual outfits. If you want to rock your boots in such a way, you should select a pair in black. Doing so will achieve a sophisticated appearance and make it easier to partner with elegant pieces. To complete the look, try pairing your chukkas with black jeans, a crew-neck T-shirt, a blazer or chinos, and a casual shirt.

Business Casual Occasions

Business Casual Occasions

Don’t just save your chukka boots for weekends and evenings out. These timeless shoes can also work perfectly for business casual looks. To nail the style, just select a pair in a dark hue and partner them with garments that are smart and sharp. A pair of trousers or chinos a white cotton shirt, and a cashmere sweater or blazer make the perfect choices to bring chukka boots into the office.

Best Chukka Boots for Men

When it comes to buying a pair of chukka boots, there are plenty from which to choose. As such, there’s a great pair of chukkas available for every gent and his style. All you need to do is find the right ones for you. Fortunately, we can help by providing you with everything you need to know to pick the perfect pair of boots. From the material and comfort level to the brand and color; here’s how to select the best chukka boots for your feet.

Leather Chukka Boots

Leather Chukka Boots

Investing in a pair of leather chukka boots is always a good idea. Leather chukkas are more durable than suede styles and will show less wear, meaning that they’ll last longer. On top of that, leather boots are also versatile and can easily work for both casual and more formal outfits. Just remember to choose a neutral shade, such as brown or black, to ensure that your chukkas are stylish and can suit any occasion.

Suede Chukka Boots

Suede Chukka Boots

Suede chukka boots are seriously stylish and essential for any modern gent. These well-loved shoes are ideal for infusing casual outfits with a smart style as well as keeping feet comfortable and fashionable. To make sure your suede chukkas suit a range of outfits, just select a shade that’s easy to match. Black, brown, sand, navy, and grey all make excellent and versatile choices. Also, ensure that you know how to care for your suede boots properly to see that you get your money’s worth.

Comfortable Chukka Boots

Chukka boots are not just stylish; they’re also comfortable, which makes them an excellent choice for gents. Of course, like all shoes, certain chukkas are more comfortable than others. So, if you’re looking for chukka boots with the best feel, try buying a pair from a trusted brand. Labels, such as Timberland and Hudson, offer high-quality boots that are built for comfort. Selecting a style with a thick sole and excellent fit will also help to keep your feet feeling fresh all day long.

READ: Best Men’s Dress Shoes You Need To Own

How to Clean Suede Chukka Boots

There’s not much point in buying a great pair of suede chukka boots if you don’t know how to keep them clean. To ensure your chukkas last a long time, clean them regularly by first stuffing them with newspaper. Then, brush off any loose dirt and gently rub any marks with a suede eraser or nail brush. Finally, re-brush your boots to raise the nap and spray with a suede protector.

How to Buy Chukka Boots

When you’re looking to purchase a pair of chukka boots, it’s important to consider both the style and the fit. To select an ideal pair, choose chukka boots that just cover your ankle and feature a close fit. When it comes to style, select either a suede design for a casual appearance or a leather option for a more formal look. Likewise, chukkas that are light in color or that feature a rubber sole will also appear more relaxed than those with a dark hue and leather sole.

How to Wear Chukka Boots

  • Select light and suede chukka boots or desert boots for a casual appearance.
  • Choose leather chukkas in dark shades for more formal outfits.
  • Partner chukka boots with jeans and a t-shirt or button-down for a casual look.
  • Wear chukka boots with black jeans, a T-shirt, and a blazer for a smart-casual style.

The Best Brands For Chukka Boots


The purist’s choice; In 1941, while deployed in Myanmar (formerly Burma); Nathan Clark, the great-grandson of James Clark (the founder of the shoe company); noticed the chukka boot variation with crepe soles and sent sketches back home. Originally, they were commissioned as lightweight; comfortable boots with rubber soles and sand-colored leather to be worn by soldiers in their downtime. It wasn’t until the 1950s that the first commercially available Clarks desert boot appeared; the style has barely changed since.

Best Chukka Boots Brands - Clarks



Heritage Northampton-based footwear firm Grenson has perfected classic British styles; and construction methods over several generations since 1866. Current chukka models hark back to the 1930s; with fine stitching giving the boots a more formal touch. Our pick is the Marcus; a classic English-style chukka boot in snuff burnished suede and finished with a tonal heel tab.

Best Chukka Boots Brands - Grenson


Young fashion footwear brand Hudson offers a comprehensive and quality selection of chukka boots at affordable price points; with finishes from polished leather to traditional suede in numerous colors including classic shades of navy, tan and black. The Ryecroft style features contemporarily burnished distressing on a slightly raised heel. Pleasingly Peaky Blinders!

Best Chukka Boots Brands - Hudson


J.M. Weston

J.M. Weston is a French luxury shoe company founded by Édouard Blanchard in 1891, in Limoges. The brand is renowned for its handmade shoes for men; still proudly made in France and as such commands a high price tag. Its casual chukka boot style features a rubber sole and unique sweeping stitching on the sides; so everyone knows you’ve invested in one of the best.

Best Chukka Boots Brands - J.M. Weston

J Shoes

Using only the finest materials and techniques, such as stacked leather soles and wall welts; J shoes has built a reputation for producing quality leather shoes in just 20 years. Founded in the East Midlands of England, the brand (once known as Journey Shoes) offers plenty of chukka choices. Its accessible prices give you the option of experimenting with several different colors, such as grey.

Best Chukka Boots Brands - J Shoes

Base London

One of the most extensive chukka boot selections available on the British high street; Base London offers an entire wall of styles in every shape, finish, and color at an enticing entry price. The retailer offers sportswear-inspired updates of the traditional chukka shape; along with excellent expressions of the classic style.

Best Chukka Boots Brands - Base London


Outdoor specialist Timberland is well known for its hard-as-nails boots. But it also turns out a contemporary range of chukkas that feature the distinctive Timberland upper. These styles have more eyelets than usual; reflecting the Timberland signature model in various finishes and colors.

Best Chukka Boots Brands - Timberland


River Island

At the more affordable end of the high street; there’s the option to sacrifice real leather for something faux and gain a greater choice of classic and contemporary silhouettes in the process. River Island is not short on great shades and finishes that you won’t be forced to choose between.

Best Chukka Boots Brands - Timberland


Red Wing

Said to last a lifetime, Red Wing prides itself on the build quality of its boots. Located in Southwest Minnesota, the brand offers an American take on this English style; with a chukka boot originally designed for indoor workers who would spend all day on their feet. Many styles are still made in the USA.

Red Wing