What to Wear with Chukka Boots: Outfit Ideas for Guys

What to Wear with Chukka Boots: Outfit Ideas for Guys

How to wear this classic pair of boots
chukka boots style guide

By Gabi Meyers | Last Updated: Feb 13 2024 | 7 min read

We love a loafer here at SG HQ. And a classic white sneaker, too. But a chukka boot just does something to us. It tugs at our style heartstrings. It’s a true men’s wardrobe staple that every guy can pull off.

And that’s why, today, I’m going to show you how to wear chukka boots in all different outfits.

In this chukka boot style guide, you’ll find:

What are chukka boots?

the boots: Mr P. split-toe shearling-lined waxed suede chukka boots, $231 (on sale)

The tl;dr: Chukka boots are ankle-high boots with suede or leather uppers, and open lacing with two to three pairs of eyelets.

If you’re wondering the difference between chukka boots and desert boots…you can think of chukka boots are an umbrella term for laced, ankle length shoes. A desert boot is characterized by its crepe rubber sole. To put it another way: chukka boots are like fruit, and desert boots are like an apple. All desert boots are chukka boots, but not all chukka boots are desert boots. Capiche?

(I’m not even going to get into Wallabee boots here, which is a post for another day, except to say they’re another stylish pair of ankle boots and you can tell them apart by their pronounced seam on the shoe’s upper!)

You can find leather chukka boots, suede chukka boots, and colors ranging from black to brown to bright green. A pair of chukka boots can be worn year round, and generally resist going in and out of fashion, making them a men’s wardrobe all-star.

Plus, they work equally well mixed into casual outfits or more formal, elevated outfits, meaning they look great with basically everything you already own.

Are chukka boots stylish?

Red Wing Shoes work leather chukka boots, $290

Bottom line? Yes!

The great thing about the footwear is you can treat them like sneakers in terms of the type of outfits they go with. Meaning? Jeans, chinos, twill pants and cords are all great options.

You can also dress them up by trading up to dressier pants, or simply choosing a pair in a more luxe suede or leather. They’ll quickly become a staple in your closet.

Chukka boots outfits

co_mongg chukka boot with jeans outfit
image: @co_mongg

Love this casual outfit featuring tan suede chukka boots with blue jeans. great for casual occasions.

The overall effect is durable style you can wear all day.

Pairing chukka boots with sturdy trousers makes for a perfect smart casual look. This outfit would work for a business casual dress code, while the creamy pink sweater and bright socks would keep you from feeling like a corporate drone.

Hugo Chegwin for Clarks Originals
image: @hugob0ssman for Clarks Originals

Love the khaki color and crepe soles on these boots. The lighter rinse jeans are totally on trend for 2024, though the outfit would look great with black jeans, too.

A simple yet stylish monochrone outfit with khakis, and #SGapproved sweater drape. love the sturdy leather sole.

You could also swap in a knit polo and unstructured blazer for a smart casual look that’s ready for the office.

Shop the best Chukka boots for men

clarks originals desert boot

Clarks Originals, $150

She’s an icon. She’s a legend. She is the moment. Clarks’ desert boot in pale khaki suede will never go out of style.

beckett simonon Laval chukka boot

Beckett Simonon, $259

The full-grain leather will develop a gorgeous patina over time, so make sure to keep them in good condition!

drakes chukka boot

Drake’s, $495

The Crosby suede chukka boots are the same style worn by Daniel Craig as James Bond in No Time To Die. Enough said.

j.crew x alden suede chukka boots

Alden for J.Crew, $696

This handsome boot is handcrafted from snuff-suede uppers and leather-lined insoles, which are super flexible, molding to your foot over time.

Ready to upgrade your style?

Ready to jump on board the chukka boot wagon? Let Team SG shop for you!

Our stylists can rescue you from shopping fatigue and sartorial apathy. We can promise the kind of personal attention and care that will make you feel like the best version of the awesome guy you already are!

We’ll also help you figure out how to wear chukka boots with everything else in your closet you already own. If you’re ready for a shopping plan that’ll save you time, energy, and your sanity, give us a shout.

Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.