How to wear chukka boots with jeans for men

Chukka boots for men are indeed versatile as we can wear them with a wide range of attires in the elegant men’s closet. Despite that, they pair better with some pants than the other. And when you think of these classic boots, nothing beats wearing them with a pair of well-tailored jeans. Classic! And that brings us to how to wear chukka boots with jeans.

Styling is endless, and every elegant man I know is always looking for a way to style what they have to look well-presented. A little addition here, a little subtraction there will give you that distinctive, handsome guy look you have always wanted after this guide.

Dust off your chukkas and let’s hop in!

What are Chukka Boots?

Before learning how to wear chukka boots with jeans, though, we need to do a few cleaning up. I mean, what are chukka boots?

These classic yet stylish boots rose to prominence as men’s fashion footwear dated to the 20th century. Since then, they’ve become a must-have for every stylish gent out there, matching them with almost any outfit in their closet.

Generally, chukka boots are ankle-high leather or suede boots with two to three lacing eyelets. Perhaps the most fascinating thing about chukka boots is their design; they’re made from two (or at most, three) entire pieces of leather material put together with lace.

You’ll find chukka boots in either leather or suede built, mostly in black, brown, and tan colors. Like other types of shoes, leather comes with more durability, while suede chukka boots can be very comfy when you wear them. Other than that, suede chukka boots pair well with business and smart-casual outfits, but they demand extra care.  

How to wear chukka boots with jeans

Straight off, get it right that you can wear chukka boots with almost any outfit in your closet. However, they’re mostly dressed casually, making them a perfect complement for jeans and T-shirts, amongst others.

But before you style them, though, here are a couple of things to know:

  1. Dark chukka boots look nice with light pants, while lighter chukka boots pair well with darker pants. So, when matching them, the contrast can improve your look.
  2. Get your jeans tailored! No, you don’t want to wear these classic boots with your jeans bottom hem widely open. Nothing beats having a well-tailored pant with a narrow leg; a wide bottom hem just doesn’t cut it.
  3. Lastly, keep your jean bottom hem rolled up above the boots. Making it cover the boot look horrible, compared to when rolled up.

With that out of the way, let us hop to the main thing. Here are various ideas on how to wear chukka boots with jeans.

Style Chukka Boots and Jeans for a Casual look

Chukka boots are more casual than formal. And when it’s time to style them with your well-tailored jeans for a casual look, there are a variety of things to throw on. However, the truth is you can’t go wrong no matter how you style them (inasmuch your picked your colors and fabric well)

Since it’s casual, a pair of tan or brown chukka boots look incredible. Just throw on your favorite pair of (blue) jeans and any t-shirt of your choice. You can also throw in a denim jacket for a more sophisticated look.

Style Chukka Boots and Jeans for a Smart Casual look

Even if you’re in for a smart-casual look, wearing your chukka boots with your favorite pair of jeans is the most stylish way to elevate your look. For this chic, smart-casual look, go for black denim jeans, a T-shirt, and complement it with dark-colored chukka boots. Finally, throw in a blazer to crank up the sophistication.

Alternatively, you can swap your T-shirt for a button-down shirt, sweater, or polo, depending on how you want it to look and perhaps, the atmospheric condition.

Style Chukka Boots and Jeans for a Business Casual look

Moving to the ultimate business-casual look, wearing your chukka boots with jeans goes up to a suitable, higher level. For that look, you’ll want to keep things sinple.

You can have your chukka boots paired with a button-down shirt and denim jeans. You can’t go wrong by adding your favorite cashmere sweater. Of course, feel free to mix things up; just make sure you’re still on the line.


As I said earlier, Chukka boots are timeless and seem not to be going out of style anytime soon. Plus, they are versatile and can make a statement out of any elegant-looking outfit in your closet.

Notwithstanding, chukka boots pair well with jeans (talk of your denim!) than any other type of pants. Once you know how to style chukka boots with jeans, you could go to any casual, smart casual, or business casual occasion without looking unkempt.

The key is to get a high-quality pair of chukka boots and take proper care of them; that guarantees you can wear them for years without looking bad. If you don’t have one, though, it’s time to stock up your wardrobe with the elegant chukka boot! Find some of the best, affordable ones 

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How to style chukka boots for men

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