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How to Wear Chukka Boots: The Only Guide You’ll Need

LA-born, New York-based lover of menswear, watches, and culture. His work is featured in many prominent menswear publications and reaches hundreds of thousands of guys every year. He knows a good boot when he sees one. Read full bio.

Last Updated: Dec 14, 2023
11 min read
Key Takeaways

For casual wear, chukka boots pair well with any well-fitted jeans and t-shirt combination. Add a third layer, like a bomber or harrington jacket, to elevate the look. For smart and business-appropriate outfits, wear darker full-grain leather chukkas. Opt for sleeker toe boxes in more formal situations.

Durable, comfortable, and stylish, chukka boots have been a closet staple since British soldiers started wearing them during World War II. Add in their popularity with aristocratic polo players and Esquire’s blessing of the original Clarks in 1949, and you’ve got footwear with the ultimate manly crossover appeal.

A lot of guys think they’re some of the best boots you can get.

Whether with a t-shirt or blazer, in suede or calfskin leather, this mega-guide will teach you how to wear chukka boots in style.

Chukka Boots vs Desert Boots: What’s the Difference?

clarks bushacre 2 vs desert boot on white background e1596230547599
Clarks Bushacre 2 (Chukka) vs Clarks Desert Boots

Off the bat, desert boots are a style of chukkas. Chukka boots feature ankle-high uppers, up to three open-laced eyelets, and either a traditional leather or suede construction. 

Meanwhile, desert boots are just earthier and more casual chukkas, featuring textured crepe soles and lighter color palettes. It’s confusing since their titles are often used interchangeably.

It’s sort of like how dive watches are a style of sport watch, but “dive” and “sport” often get used interchangeably (technically wrong) or as a different category (not technically wrong, but confusing). This happens because, since the Submariner came out, dive watches have become ever-present. Similarly, since Clarks Desert Boots were introduced in 1949 as the world’s first chukka, they’ve become an iconic and common variation.

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To summarize: not all chukkas are desert boots, but all desert boots are chukkas.

When to Wear Chukka Boots


Author William Barton modeling Thursday Boots Scout chukka in mocha weathersafe suede

As long as the pieces in your outfit fit properly, you can wear chukkas on any occasion you’d usually wear sneakers—besides the gym, of course.

Chukka boots elevate a simple shirt and jeans combination, especially if you add a third, outer layer to match the boots’ outdoorsy aesthetic.

With a Relaxed Textured Sweater

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That this look is so easy and simple is what makes it work so well. It’s really just a t-shirt and jeans partnership, souped up with layers and accessories. 

Texture always goes well with rugged chukkas, and this sweater checks that box while giving the outfit a hip sophistication that doesn’t try too hard. Same goes for the mint-dialed wristwatch, simple bracelet, and sunglasses. 

Suede chukkas could have worked in this situation just as well, but the leather levels up the look as do the black pants.


You can pull off any material and color chukka boots with a smart casual outfit, as long as you’re striking a good balance with all of the pieces.

This same look works if you’re wearing Chelsea boots too, but there are some big differences between chukkas and Chelsea boots.

If you’re going to go with a casual napped brown shoe, go more conservative and formal with the pants and shirt combo, then maybe top it off with rugged accessories like a worn leather-strapped watch or a hunter’s jacket.

With a Pullover, White Trousers, and Hooded Utility Jacket

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The canvas of this outfit is super preppy: Black pullover, an oxford blue dress shirt, and white trousers. This gives us room to go hardcore woodsman with the shoes and accessories. 

Enter the brown suede boots and the weather-conscious, hunting-appropriate jacket.

This combo fully follows the strike-a-balance rule when incorporating chukkas into a smart casual outfit. It can take you from a Friday work meeting to a pheasant hunt at a countryside estate.

Thursday Scout in Cognac Suede

The Thursday Scout is one of the best bang-for-buck chukkas on the market. With Thursday's proprietary leather and a Goodyear welt, this boot is hard to beat for value. If you're looking for a stylish, slim, casual chukka, the Cognac Suede version is often our go-to recommendation.

Check Price

Monochromatic Combination With a Plaid Statement Jacket

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This autumn palette outfit has an outdoorsy vibe with a hint of Ivy League sophistication. The suede black chukka is an excellent pairing because the napped aesthetic matches the Americana feel, but the dark shade is chic and seasonal. 

The well-structured plaid coat is obviously the star of the show, but wouldn’t be as effective without the thoughtful monochrome canvas. 


For business appropriate looks, stick to leather chukka boots with a sleek or pointed toe box and dark uppers of either suede or leather. Leather outsoles are the safest bet, but it all depends on how you’re striking that balance again. 

Of course, always consider the culture of your office and your clients.

Contemporary Business Look

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This look combines classic pieces from different business traditions and reimagines them into modern fits, making it the perfect outfit for minimalist leather chukka boots.

The striped shirt has a long button-down collar reminiscent of 80s Wall street, while the tie is a preppy club style. However, the black jacket and gray pants have a box-cut modern fit a la Thom Brown for a youthful spin.

Thursday Scout

The Thursday Scout is one of the best bang-for-buck chukkas on the market. With Thursday's proprietary leather and a stitchdown construction, this boot is hard to beat for value.

Check Price Read Our Review

Friday Business Look

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This combination is all about the accessories. The normal-fit dark shirt and light pants partnership is great for warm weather or Friday situations. 

The normcore understatedness gives him room to have fun with the extras: Stylish browline sunglasses, a fashionable multi-compartment briefcase, and of course, suede charcoal chukkas with white outsoles.

With a Harrington Jacket and Jeans

Typically, black and brown are a risky combination, similar to gold and silver. The tawny-shaded chukkas with this mostly monochrome number work perfectly, because the blacks are a lowkey dark navy. 

Every navy piece up top has a slightly different texture, so the napped suede shoes are on theme. Add the peaking plaid from inside the jacket and you’ve got an undercover Bond look with a pop of color.

When Not to Wear Chukka Boots

These days, chukka boots can be worn in most sartorial situations, depending on their construction and color. For example, you can wear chukkas with a black suit, but don’t wear tan suedes with a crepe sole. You can partner them with shorts in the summer, but don’t choose overly dressy full-grain leathers in all black.

When it comes to professional situations, it all depends on your office dress code or who your clients are and where you’re meeting them. Are they a hip t-shirt-and-jeans startup and you’re meeting after hours at a lounge? Then chukkas are a fine choice.

There are only two hard nos. Don’t wear them at the gym, of course. And don’t combine them with a traditional all-black tuxedo at a formal and conservative event.

How to Wear Chukka Boots with Jeans: 3 Stylish Looks 

model standing on staircase wearing beeswax color clarks desert boot leather chukka

Pairing chukkas with jeans is one of the most exceedingly versatile combinations. It’s an effective canvas to experiment with shirts and outer layers on.

For a casual look, you can top off a brown suede/blue jeans pairing with any old t-shirt, button-up, or henley. You can even go for an oversized scoop neck shirt and well-fitting blue jeans and trendy chukkas will anchor the whole outfit.

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For smart casual looks, you can basically choose any style of chukka boots, as long as the whole outfit is balanced—seeing a theme? For example, you can wear desert boots, but pair it with dark selvedge denim, a nice button-down, and a blazer. The more formal the situation, the darker your jeans should be and the pointier the toe box of your chukkas should be.

Elevated Casual Outfit

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This outfit is a perfect example of how a third layer, boots, and accessories can elevate a simple combination. The dark jeans and t-shirt alone would have been uninspired, but by tucking his shirt in, he is able to color-match a belt to his brown chukkas, and leather strapped watch. 

Moreover, very little shade variation is happening here, for a streamlined and clean look that looks casual and effortless.

All Denim Look

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How do you pull off an all-denim look without looking like a cowboy? With different-colored denims, a minimalist modern watch, and cool chukkas. 

The loose and worn brown suede boots go well with this western-inspired style because the jeans are really fitted, which brings the whole look into a modern and urban realm of fashion.

Dapper Jeans Outfit

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The sum is greater than its parts in this outfit, and that’s what makes it so trend-resistant. The jeans are perfectly fitted, not too tight or too loose since either would be too youthful for this grown-up, put-together look. Even the pocket square doesn’t look over-the-top because of its understated hue. 

The chukka boots are purposeful, and feature subtle pebbling without being overly-polished. In fact, none of the pieces are too fancy. It’s the well thought-out combination of specific items that makes this outfit fancy.

Types of Chukka Boots and Our Top Picks

Leather Chukka Boots

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More formal and durable than their suede equivalents, leather chukka boots are a versatile piece of footwear that can easily be worn everyday. High-quality full-grain leather chukkas develop a sophisticated patina over time, and will last you several years. Polished boots look more elegant, while slightly-worn boots look more adventurous. 

In more formal settings, definitely opt for leather outsoles. Crepe soles and rubber soles are perfectly acceptable for smart casual situations or professional casual Fridays, as long as the sole has a pronounced heel.

Suede Chukka Boots 

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Suede chukkas are more casual-looking than traditional leather ones. Yet, their napped aesthetic is still distinct and luxurious, making them the perfect way to level-up relaxed looks.

Suede is also fashionably seasonal for spring and summer. The texture and softer look of its surface looks great with lighter colors and flowy summer shirts.

Just as with the leather versions, boots with more pronounced heels are more formal than those with flatter crepe and rubber outsoles. 

The traditional desert boot features a suede upper, and is often associated with a cool, adventurous look. As such, they go well with field watches that have a military aesthetic.

Top Recommendation: Thursday Scout

Thursday Boots’ chukka, the Scout, sports the beautiful napped look we expect from a topnotch suede shoe. It’s made out of Thursday’s WeatherSafe suede collection, which means it was treated with their waterproof and hydrophobic compound solution for effective water-resistance. So not only are they soft and springy, but strong and long-lasting. 

As a company, Thursday Boots gets bonus points for focusing on fair labor and sustainability as well. 100% of their bovine leather comes from Tier 1 USA cattle and they receive high marks from the Leather Working Group, which rates environmental practices and chemical management.

Thursday Scout in Cognac Suede

The Thursday Scout is one of the best bang-for-buck chukkas on the market. With Thursday's proprietary leather and a Goodyear welt, this boot is hard to beat for value. If you're looking for a stylish, slim, casual chukka, the Cognac Suede version is often our go-to recommendation.

Check Price


Can you wear chukkas with dress pants?

Yes, you can wear either leather chukkas or dark suede chukkas with dress pants. For the most formal occasions, choose leather outsoles and pointed toe boots.

Can chukka boots be worn in the summer?

Yes, suede chukkas boots in lighter hues like tan, buff, white, and light gray are excellent style choices for the warm seasons. Summer is a great time to wear desert boot style chukkas.

What socks do you wear with chukkas?

Wear cotton or wool socks that match your trousers if you’re going for a more traditional look. For a bolder approach, choose brightly colored or printed socks that match or complement another piece of clothing or your accessories.

Why are they called chukka boots?

Chukka boots resemble the jodhpur boots that polo players wear. The word chukka comes from the game of polo, which is a period of play.


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