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Chukka boots have been around for many decades, making it a bit intimidating to style. So I've chosen four of my favorite brands and styles of the amazing Chukka boot to style. These boots are in order of appearance. To get started let's give a little history on the Chukka boot…

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The Chukka (pronounced Chuk-ka) boot has a pretty interesting history. The name is believed to be derived from the seven and a half minute Polo playing period called a chukka or chukker. The term itself is actually derived from the Hindi word ‘chukkar’ meaning ‘circle’ or ‘turn’. Another opinion is that the chukka boot received it’s name due to the resemblance of the boots polo players wore. Chukka boots strongly resemble the Judhpor boot so it's a great assumption that they originated in India amongst the British Army. A proper chukka boot should reach the ankle and no further. They should have two or three lacing eyelets; anything else is not a chukka boot.

#StreetStyle Casual

Now that we’ve learned the history of the Chukka boot let's get into the many varieties of the Chukka boot and how to styling them. Sporting a shoe with so much history and another generation can be daunting for some. So I’ve taken the liberty of putting together some looks to show you just how easy it is. It was also very fun.

Apollo Chukka Boot

I decided to start with the most modern version of the Chukka boot. The #streetstyle look is so hot these days that I had to give you readers two style ideas just so you could see how transitional these shoes really are. Let's take the Apollo Chukka Boots by Native and simply pair them with a denim sleeved shirt and skinny jeans. Now it's up to you on weather you want to raise the hem on your jeans by rolling them up. With these mid-top shoes I wouldn't go any higher than the ankle. Most likely mid-ankle as shown in the picture above would work perfectly.

Again because I loved the Apollo boot by Native so much I had to give you guys a second look. With this look I wanted to give you a street style that is more out together and great for a night out, partying with friends, or simply university classes. Let's lighten the trousers to let the Chukka boot pop. The focal point for this look are the shoes, ray ban sunglasses, and Mickey Mouse backpack by Herschel Supply Company all of which I will link in. Now it's cool to sport color every now and again.

Understandably the gloomy weather in London, NYC, and everywhere else during the fall/winter seasons can bring out the navy’s, Browns, and blacks so why not change things up a bit with this red plaid shirt. You can either wear it as pictured or tie it around your waist and sport a white tee shirt.

Basics of Prep

We’ve covered a nice casual street style look. So let's prep it up a bit shall we? Okay so with this nice brown suede boot let's play with texture & add a pop of color. Many people find brown to be boring but it's quite the opposite if you know how to style it up. My first tip would be the trousers. I spotted these maroon chino pants (dickies are also appropriate) and instantly created this preppy autumn look. Once you have your base color (reds, greens, & yellows all pair with brown nicely) you dress up. I added a simple white shirt because I didn't want to take away from the boots or the trousers. To finish the look add texture with a nice leather backpack and leather wrist band. If you notice the different shades of brown to keep the look from being stale yet it's not overwhelming.

Clarks Original Desert Boot

These Clarks Original Desert boots are as close to the original Chukka boot one may get. Over the decades the Chukka boot also known as one of the original desert boots has changed in the textiles used for creating this amazing shoe. Remember the original Chukka boot was only crafted with leather or suede.

Because the chukka boot is so popular they're great to sport with any look. For instance if you want to rock your boots in the office- simply pair a nice pair of brown suede/leather chukka boots with a grey (preferably wool or tweed) suit. Not only will the shoes pop but it gives you a bit of texture. One thing about textured shoes and clothing is that it adds a sense of pride to one's look. It's not simple but then it's not over the top.

Leather Chukka Boot

I call this look Chelsea Style because it's posh yet still inviting. Take these gorgeous dark brown leather boots by Clarks and dress them up with a navy suit (tailored of course) added with either this simple grey turtleneck. To dress the look up even more I’d sport the boots and navy suit with a crisp white button down shirt and tie. Let's not over accessorize this look so a nice dark brown satchel/briefcase as close in color to your boots will work perfectly.

When wearing chukka boots it's best to tailor your trousers. The bottom of your trousers should not be too wide as to not hide the boot itself. Clarks version of the chukka has great craftsmanship on their boots. Great leather that's durable. And as the boots weather they look even better.


* Tailor the suit.

* Always pair brown shoes with a brown belt.

* Add a pop of colour with your socks, tie, and pocket square.

Houghton Suede Chukka Boot

Most people think that suede is too rich a fabric. As in you have to dress it up anytime you wear the fabric. One thing I love about Chukka boots is that they defy the rules. You can't truly rock them any way you please. So far I think you've guys have gotten the idea. But just incase I'll give you one more example of how to style with these light brown Chukka boots by Hudson.

One look we haven't covered is the always hip biker/mod style. You may wonder how you can sport brown suede Chukka’s with edge so here's the perfect example. To start grab your Houghton Brown Chukka’s by Hudson, pair them with either black skinny it slim fit jeans. Ripped jeans even better. I wanted a bit of pop but to stay in my color scheme so a spotted shirt will do the trick. Again with this a torn sweater or distressed shirt all works. Now throw on a leather bomber and Ray Bans to add that extra touch of bad boy and you're set. A nice fragrance of your choice should always follow and look. One of my favs is this Amber fragrance. Subtle tones of spices and wood giving off hints of the British Countryside. With any fragrance apply behind the knees & back of the neck. That way the aroma rises through your body with your body heat and you're not directly hitting people with your smell.

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