How to Style Chukka Boots for Men

Few boots look better than the chukka.

It’s sleek, has a beautiful silhouette, and is perfect for the fall and winter.

It comes in a variety of colors and materials that are sure to give a boost to any outfit.

If you are a shoe snob and want your collection to be complete, then chukka’s need to be on your list.

This guide is going to teach you how to style chukka boots, what to wear with them, and includes answers to questions you might have about this awesome footwear.

How to Style Chukka Boots for Men

What Are Chukka Boots?

You may get confused trying to figure out what chukka boots are with so many designs on the market.

Chukka boots are no new name to the shoe world, though. They have been trendy for a very long time and are a staple in menswear. They are an ankle-high pair of boots that is made of leather, suede, or canvas in some cases. They typically have two to three eyelets, accompanied by thin laces. Some brands have begun adding more eyelets, but the original design sticks to just a couple.

The boots are typically constructed of two panels of leather to form its iconic shape. The quarters of the boot are neatly sewn on the top of the vamp. Their open lacing and thin soles make them easy to classify from other shoes.

It’s easy to mix up the chukka and desert shoes, though — I do it all of the time! But, desert boots have a crepe rubber sole and were inspired by British military boots.

Where Did Chukka Boots Originate?

Did you know that there is a seven and half minute long match in the game of polo called chukka? It actually plays into how the boot got its name.

There are many theories about how the chukka came to be. One is that the polo players in India used these boots as a predecessor to the actual polo boots they used during matches. They would wear these boots off the field, as they were comfortable and very versatile.

In Indian polo traditions, chukker means circle or urn’. During the Second World War, these styles of boots were worn by the British soldiers in the deserts, hence the desert boot like the famous Clarks.

When the British saw the local Indians sporting these boots, they took note and brought some of them back home. Slowly they began to be designed by modern shoe companies.

If this wasn’t enough, chukkas gained extreme popularity when the Duke of Windsor started wearing them in the 1920s. His outfit is a hint to a further question I’ll be answered later

How To Wear Chukka Boots With Jeans

Chukka boots are the most versatile pair of boots you can own. I would argue that they look the best with jeans, but you need to know what to wear with them to maximize your appearance. Whether it be a casual day out, a night at the office, or a dinner with your spouse, chukka’s will never disappoint.

One of the cleanest ways to wear chukka boots and jeans is with a crisp dress shirt and denim jacket.

Shop The Look

Throw a scarf over with a contrasting color or pattern to add texture. This will keep you warm and you’ll easily be the best-looking guy walking down the street. A chronograph watch pairs with this look nice since it’s not overly formal.

Going to work? Meeting with a client? Just want to look sharp? Then try mixing your boots with jeans and a blazer for a snazzy business casual outfit.

You can wear a t-shirt under the blazer, or stick to a simple dress shirt. Blue denim jeans with a simple wash are ideal. This is business casual at its finest. Oh, and remember this one rule — the simpler the chukka boot, the more formal it is. That means for this look, it’s wise to stick to a brown or tan chukka boot that has two eyelets. When jeans cover the top portion of the boot, it resembles a dress shoe more than anything!

Your skinny jeans can also be paired with a pair of chukka’s. It gives off a modern and youthful look. Wear a sweater or hoodie on top to make it into a casual and laid-back outfit.

Over top, a pea coat or overcoat will be a nice addition. A messenger bag or backpack will finish it off and give you room to store the essentials. This is a great idea for students or young gentlemen that hustle to work every day.

The material you choose is also very important. In general, suede tends to be less formal and will require more upkeep. In the fall and winter, water or snow can easily damage the suede. Invest into a shoe spray to protect your chukka’s and avoid any wet areas when you’re out and about. Sometimes style comes at a cost Standard leather-like full-grain or calfskin is more ideal because it’s durable and can take more of a beating with less maintenance. But, always take care of your shoes and they’ll take care of you.

How To Style Brown Chukka Boots

Brown is one of the best colors in fashion. Period.

What doesn’t match with brown? I can’t think of anything!

That’s why I recommend buying a pair of brown chukka boots if it’s your first pair. When you’re more advanced, red, navy, olive, and other colors can be added to your style arsenal. I would say tan is on par with light or dark brown, by the way.

If there’s one color that pairs effortlessly with brown, it’s blue. Try wearing blue jeans and a blue peacoat like the below gentleman and tell me you don’t smile when you look in the mirror.

White is a good base, so personally, I enjoy putting on a white t-shirt, dress shirt, or turtleneck with something like this. Grey or a contrasting color like red could work, too. I highly suggest that you learn some color palettes if you haven’t already. It will transform your fashion sense and people will ask if you work for GQ because you’ll look so good.

If you are going out for dinner or need a formal outfit with brown chukka boots, try wearing a sports coat with navy chinos. The brown and blue as I mentioned make the perfect blend, and it leaves you with the opportunity to have some fun with your coat. A houndstooth or twill pattern is something to consider.

This leads me to the next question, which if you remember I hinted to with the Duke of Windsor earlier.

Can You Wear Chukka Boots With A Suit?

It’s a general tendency to think that chukka boots are only meant to be worn with jeans or casual wear. But, rules were made to be broken. And that means that chukka boots can definitely be worn with a suit. But hold your horses. If you’re going to be a fashion rebel, you have to still do some things right.

You want simple chukka boots with specifically two eyelets. They should have a slim silhouette that looks close to a dress shoe when your suit pants cover them. Opt for calfskin leather and avoid suede. Brown or tan is ideal, as other colors swing more on the side of being informal.

Can You Wear Chukka Boots With Dress Pants?

Yes, you can absolutely wear dress pants with chukka boots. You just have to pay attention to detail. Your dress pants should be nicely tailored with little to no slack, which allows the chukka’s to sit nicely under the hem.

Try wearing tan suede chukka boots, navy dress pants, and a white dress shirt tucked in. Make sure to match your belt to your shoes and top this off with a contrasting tie. Red comes to mind first, but patterns and interesting designs aren’t out of the question. Bring your suit jacket along if it’s getting cool or you need to head into a meeting.

Can You Wear Chukka Boots With Shorts?

I have to backtrack a bit here. I said rules were made to be broken, and they are. But, boots just don’t look good with shorts. They scream that you don’t understand basic fashion etiquette. Chukka’s should be worn exclusively with pants. That means jeans, chinos, wool trousers, and suit pants. If you’re thinking “What about my clown pants?”, save those for the weekend

Are Chukka Boots Formal?

Chukka boots are a nice mix between relaxed and formal. They’re a tool in your wardrobe and a tool is only as good as you how to use it. This means that if you style it correctly, these boots can be very formal or very casual.

I touched upon this earlier, but let me reiterate. Simpler footwear is always deemed higher on the formal scale. Think wholecut oxfords versus brogues. When you begin adding more flare and designs, it’s just not as professional-looking. The same goes for boots.

Suede chukka’s and fun colors are good for business casual and chill outfits. But, you probably shouldn’t wear them to the office or at a wedding. Brown, tans, blacks, and high-quality leather is the name of the game.

Are Chukka Boots Good For Winters?

If there’s one reason I look forward to sweater weather, it’s because I can layer and finally bring out my favorite boots. It goes without saying that chukka boots are awesome for the cold weather. They’re stylish, keep your feet warm, and they aren’t too bulky. Good pairs will have comfortable soles and breathable lining.

On the flip side, the winter can be the greatest enemy to your chukka boots. Snow, water, and slush are not a good combination with leather or suede. It can leave spots, try it out, and damage it over time. I like to bring mine out on days when the weather isn’t too bad. After a snowstorm? Probably not. When the sun has melted away a lot of the snow and it’s nice out? Spot on!

Are Chukka Boots Good For Hiking?

Chukka boots are purely for fashion in my opinion. Sure, they started out as an athletic piece of footwear and even the military adopted them. But, it’s just not what they are meant for in modern times. If you saw someone with a beautiful pair of suede chukka’s in the middle of the forest today, you’d think they’re crazy. I know that I would.

If you’re hiking, you need a boot that you can beat up, that resists water, and that you don’t mind getting dirty. Timberland has some great hiking boots and most outdoor brands will carry similar models.

Summing All Of That Up

Chukka boots need to be in your closet for the fall and winter. They can be worn with jeans for business casual outfits or with a suit if you’re meticulous about styling them.

Who would have thought that a boot which started out for the game of polo and later used by soldiers would become a fashion staple?

Stick to brown or tan for the most versatility. Olive, navy, and oxblood are other color choices I’d recommend if you want to add some personality to an outfit, though. Take the time to clean them on a regular basis with a brush and leather conditioner. Suede will need extra care and it’d be in your best interest to buy a protective spray.

How do you like to wear your chukka boots?

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