How to Wear Chukka Boots
Haley Snow
Table of Contents
If you’re wondering how to wear chukka boots, the truth is that they are incredibly easy to wear. They’re comfortable and durable and, depending on the materials and colors you choose, they can be worn with just about anything.
A staple in menswear since the early 20th century, chukka boots have persisted due to their versatility. They are the perfect mix of style and function—as if a boot and a dress shoe had a baby and named it ‘Chukka.’
Once you’ve decided to invest in a pair, the next natural step is to figure out how to wear chukka boots. Luckily for you, there aren’t many restrictions when it comes to styling these boots.
To wear chukka boots well, you’ll need one very important thing—a good tailor. Why do you need a tailor to style your boots? Well simply put, the length of your hem is going to make or break your chukka boots outfit.
Because they come up the ankle, and the lacing detail is located at the topline, having a sloppy, long hem will ruin the look.
Having properly altered clothing is an important step for anyone building a designer wardrobe and it’s a key component when figuring out how to wear Chukka boots. So invest some time in finding a good tailor or seamstress.
Tailoring clothing is an art and, unfortunately, the industry seems to be going the way of the cobbler.
Now that we’ve gone over the need for a clean, unbroken hem, there are many ways to style chukkas. When worn with well-tailored suiting, sleek socks, or bare ankles, the chukka boot gives your outfit more dimension than your average dress shoe.
While originally designed for men, the chukka boot is an excellent option for women as well. Women can wear them with trousers, denim, or even dresses. The chukka boot can add an edge to an outfit that you may have otherwise paired with dress shoes or sneakers.
What Are Chukka Boots?
Before we learn how to wear Chukka boots, first we must know what they are. So what are chukka boots? Chukkas are a low profile, ankle height, and laced boot. They’re similar to the desert boot, both having similar silhouettes and double eyelet lacing systems.
However, chukka boots are often more structurally sound, featuring sturdy leather as opposed to the soft suede associated with desert boots.
Both have their roots in the military—something quite common in menswear. Yet chukka boots are notably dressier, mostly due to the leather used to create them.
Chukka boots were made famous by the ‘almost’ King of England, Edward VIII after he began donning the style in 1924. Edward was the eldest son of King George the V and Mary of Teck.
He is best known for his role in one of the greatest scandals of the 20th century. His choice to abdicate the throne and marry a divorced American woman (Wallis Simpson), set the course for Britain’s current and longest-reigning monarch, Queen Elizabeth II to take the royal seat.
His impact on the world at large is of course far larger than popularizing a style of boot. Yet his affection for the style is likely what cemented them in fashion history.
Edward VIII wore chukka boots regularly and with varying outfits. He wore them with both dress and casual wear, proving to the world how versatile this style of boot truly is.
And now that you know a bit about the history of these boots, you might be wondering where the name ‘chukka’ came from. The exact origin of the name cannot be confirmed.
However, it’s highly likely that it came from the game of polo. What is a chukka? A ‘chukka’ is what polo players call a period of play.
When to Wear Chukka Boots
Wondering when to wear your chukka boots? When to wear them is just as important as how to wear chukka boots. Depending on the season, the occasion, and your personal style, the answer can vary.
Can chukka boots be worn year-round? The answer is “yes.” Chukka boots can be worn in autumn, winter, and spring, depending on the warmth of the lining and the tread of the sole. We’ll take a closer look at this topic below.
- Winter: Many brands like Le Canadienne and Canada Goose have introduced winter chukkas into their product lines. Often lined with shearling and featuring a thick rubber tread, these are a notably cute option for a winter boot.
- Spring: The rainy days of spring also require a certain amount of water-proofing. Choose a leather pair with a rubber outsole, then be sure to protect your leather with a waterproofing spray.
- Summer: While chukka boots look great with many lightweight summer outfits, you might prefer wearing something a little more breathable when the temperature and humidity start to rise.
- Autumn: Fall, in our opinion, is the ideal time to wear your chukka boots. This is the season that most reflects the classic look associated with the chukka—slim outsoles, rich cognac leathers, and little to no lining. Fall is also the season of the flannel, the cardigan, the wool jacket, and all good friends of the chukka boot.
Next, we’ll discuss the topic of occasions. There are few occasions where the right chukka boot wouldn’t be appropriate. After all, these are versatile boots.
And since they’re usually a neutral color, they will complement so many ensembles. So unless it’s a black or white tie affair, odds are your chukkas are invited to the party.
Whether you’re running errands, going out to dinner, heading to a party, what have you, the chukka boot will be welcome. When paired with the proper accouterments, the chukka could become your new wardrobe basic.
Below you’ll find outfit ideas that will have you taking your chukka boots out of the box and out on the town, no matter the occasion.
While we featured lots of casual outfits with chukka boots, we’ve also included some dressier, formal options. Hopefully, after viewing these looks, you won’t be wondering how to wear chukka boots anymore.
10 Outfit Ideas With Chukka Boots
This first outfit is a quintessential ‘how to wear chukka boots in autumn’ look—note the pumpkins and potted mums in the background.
It’s also a great way to wear casual chukka boots. The navy crew neck sweater, rich olive pants, and light grey chukka boots create a muted, but colorful look for the fall.
Plus, leaving your ankles bare creates a nice break between the top of the boot and the hem of the pant, making this look cool and casual. It really is a perfect men’s casual chukka boots style.
When considering how to wear chukka boots with suit attire, use this as an example.
Here we have chic suiting with an unexpected twist. By pairing brown suede chukka boots with a sleek double-breasted navy suit, this gentleman has taken something relatively traditional and made it modern-day-cool.
Donning a brown watch or bag would add even more dimension to this already hip ensemble.
Now, these are some fabulous chukka-style boots. While they don’t feature the traditional double eyelet laces, they still maintain that classic chukka styling.
The shearling lining and rich navy suede give them the feeling of a slipper. Yet the insole and mid-sole make these true boots.
Paired with monochromatic trousers and what one can only assume is a luxe cashmere sweater, this chukka boots style is laidback luxury at its finest.
If you’re wondering how to wear chukka boots with jeans, this is an excellent example.
This is ruggedness at its finest. Everything in this outfit, from the wash of the denim, and the Henley collared sweater to the braided belt and worn-in leather jacket screams urban cowboy.
And the perfect way to complete the ensemble is with a classic, brown pair of leather chukka boots.
This is an unexpected but delightful way to wear chukka boots. By pairing them with a short, flouncy dress, the model has made the boots seem quite feminine.
Another factor that makes this look work is the color palette. By keeping the tones similar, the more masculine structure of the chukka boot is minimized, making the look more composed.
Let’s be honest, ankle boots and short dresses aren’t always an easy look to pull off, but she does it perfectly.
Here we have the urban cowboy’s well-suited metropolitan friend. With this traditional suit, complete with pocket square, tie, and tucked scarf it may not seem obvious to add a chukka boot.
However, the rich chocolate brown suede of the boot is just as luxurious as the suit itself, making the whole ensemble work incredibly well. It’s also a great example of how to wear chukka boots with elegant, formal attire.
If you’re still unsure how to wear chukka boots, ladies, here’s another outfit idea for you.
As we mentioned previously, chukka boots have historically been a male style. But as fashion gradually becomes degendered, those old school rules will no longer apply.
We adore this monochromatic look, complete with an oversized shirt, roll-cuff cargos, chukkas, and plaid socks.
Chukka boots and dresses go surprisingly well together. These olive green chukkas and the green floral dress pictured here are perfect examples of how to combine the masculine and feminine—projecting beauty and utility in a simple two-piece outfit.
Here’s another casual chukka boot outfit. This one includes denim jeans and boots—the best of friends.
Topped with a white tee and blazer, the chukka boots and jeans steal the show here. Cut with a raw, fraying hem, the denim really allows the boot to shine.
What Type of Chukka Boots Can You Get?
Chukka boots come in many different variations. As we mentioned before, there is the classic, slim-soled chukka. But there’s also the winter chukka, often made of nubuck suede and lined in shearling, giving the classically slim profiled boot a notably chunkier quality.
If you live in a relatively dry region of the world, choosing a suede chukka is a great way to soften the style of the boot and give it a slightly prettier feel.
Chukka boots come in many colors—black, sand, olive, and cognac to name a few. However, we’re always suckers for a classic, so a chukka crafted from sturdy cognac-colored leather will forever be our favorite.
How to Style Chukka Boots
The options here are endless. Pairing the chukka with denim and flannel elevates the classic look to a more chic, urban version of lumberjack wear. As an added bonus, no hemming is necessary—simply cuff your jeans.
Adding a sleek pair of chukkas to a suit is another great way to style these boots. Just be sure to keep the colors within the same family.
For example, wear a navy suit with black chukkas and a black belt. And if you wear a light grey suit, pair it with a cognac pair of boots and a matching belt.
While chukka boots have historically been a male footwear style we, as modern women, simply couldn’t allow that. Our favorite way to style women’s chukka boots is with a thick calf-length sock and a knit dress.
The blending of masculine and feminine energy in an outfit like this creates a comfortable and beautiful look.
Of course, women can wear chukkas in the same way that men can—with jeans, a tee, and a jacket. Or, they could even wear them with a monochromatic suit.
Fashion Tips to Avoid With Chukka Boots
To keep you looking your best when you wear your chukka boots, we’ve compiled a list of fashion no-nos you should avoid.
- Elongated hem: As previously mentioned, the most important thing to avoid when styling chukka boots is an elongated hem. The charm of chukkas lies in the detailing at the top of the boots, so to cover it with ill-fitting trousers would be a waste.
Not to mention the fact that allowing the bottom of your trousers to break on the top of your shoe will do harm to your pants and add extra wear to your shoe, especially if your chukkas are suede.
- Shorts: Other than in a few instances, like the outfit you’ll find pictured at the end of this article, chukka boots and shorts aren’t usually the best of pals. If this is an outfit you insist on trying, be sure to channel the bohemian urban-outback look to pull the ensemble off.
- Formal and athletic venues: Since chukka boots are so versatile, it would be hard to make a mistake when styling them. The only real no-nos are so obvious it feels silly to even write them down.
Chukka boots are not welcome at a black-tie affair, and they are obviously not welcome at the gym. Although I’m sure (and hopeful) that you already knew that.
How to Take Care of Chukka Boots
Taking care of chukka boots is no different than caring for any fine leather goods. The first consideration is whether or not you’ve chosen to invest in suede or leather.
A few drops of Castile soap, warm water, and a microfibre cloth are really all you need to keep your leather looking fresh.
When it comes to suede, using a dry suede sponge or white vinegar with a clean cloth to wipe your chukkas is the safest way to remove any imperfections without damaging the material.
Also, it’s always important to pre-treat your footwear with a protective spray. When it comes to boots, KIWI tough silicone protective spray is a great option. It’s inexpensive and provides a significant shield against dirt, water, and salt stains.
Best Places to Buy Chukka Boots
Now that you know how to wear chukka boots, if you’re ready to buy a pair now, here are some awesome retailers to check out.
- SSENSE: SSENSE is always a great place to start when you’re looking for anything designer. Its interface is simple to use, and you’re bound to find what you’re looking for and likely more.
- Shopstyle: Similar to SSENSE, Shopstyle has styles from every designer imaginable. It’s like Charlie’s Chocolate Factory for designer goods, and it has a wide range of chukka boots available. However, there’s no golden ticket, so warn your credit card before entering.
- Timberland: Few brands are as synonymous with boots as Timberlands. A cultural favorite, Timberlands are not only a beloved brand, but they also make sturdy quality boots.
- Farfetch: This is another e-commerce site with a wide breadth of merchandise. SSENSE, Shopstyle, and Farfetch are all great places to explore if you’re unsure of what kind of chukka boot you’re looking for and if you’re after some ready-to-wear items to accompany your new footwear.
- Clarks: Clarks are sort of the OG of the chukka and its cousin, the desert boot. Known for their superior quality and classy craftsmanship, Clarks is the place to go if you want that classic ‘Duke of Windsor’ style.
- Mr. Porter: Mr. Porter is a great place to find high-end designer chukka boots. They feature chukkas by Tom Ford, Manolo Blahnik, Brunello Cucinelli, and John Lobb. So if you’re looking for the best of the best, Mr. Porter is the place to go.
Final Thoughts
The chukka boot is a century-old menswear staple that has maintained its style, shape, and versatility throughout the years. While there are small variations in the modern styles, the chukka boot has remained the same, even as fashion and trends have evolved.
These tried-and-true styles are the foundation of modern dressing. And they’re the perfect wardrobe staple to add to your shoe collection. That’s because the chukka boot is such a versatile, well-made shoe. Plus, you’ll never have to worry about these boots going out of style.
The most difficult section of this article to write was the ‘what to avoid section’ because these shoes really can go with anything—so long as you have the right vision when putting your look together.
Chukka boots can be almost anything and everything you’d like them to be. The fine craftsmanship ensures that you’ll get to enjoy them for years to come. So, if you happen to be in the market for a new pair of all-around boots, invest in a pair of chukkas. We promise you won’t regret it.
Wondering how to style other types of boots? Check out these helpful guides:
