We don’t really believe in hard-and-fast rules around here when it comes to style — so much of it comes down to personal taste, after all. So we’re not going to say something like, “Every man absolutely needs to own a pair of chukka boots.” But what we will say is that chukka boots are an incredibly versatile style of footwear that you’ll definitely get a lot of use out of. That is, as long as you know how to wear them. It’s a lot to consider — luckily, we’ve already done the legwork and picked out the best chukka boots for men right now.
Good news on the styling front, too: If we had to use one word to describe chukka boots, it would be “uncomplicated.” Thanks to its clean lines, timeless silhouette, and laid-back styling, chukkas look pretty damn handsome paired with anything on the casual side of the spectrum. Whether you’re sporting a relaxed weekend warrior ‘fit or headed out to a more business casual occasion, you can’t go wrong lacing up a pair of chukka boots.
Before we head into the ins and outs of wearing chukka boots, let’s do a quick rundown on the style for the uninitiated. Generally speaking, the term “chukka” refers to an ankle-high leather or suede boot with open lacing and two or three pairs of eyelets. But that doesn’t exactly narrow it down, does it? What you’re really looking for is the style’s signature design, made from only two or three pieces of leather and tied up with a thin lace.
If you’re wondering where the name “chukka” comes from, you’ll be disappointed to hear that no one’s entirely sure. The most accepted theory is that it comes from polo, where a chukka refers to a period of play, like an inning or a quarter. But the jury’s still out on that one.
Finally, there’s the question of whether there is a difference between chukka boots and desert boots. The answer: yes and no. In actuality, desert boots are a type of chukka that’s crafted with a crepe sole and a suede upper. The style was made popular by Clark’s after WWII, and it was based on the boots British soldiers wore in, you guessed it, the deserts of Africa.
Choosing a pair of chukka boots requires considering a couple of factors. First up, there’s material. Do you want to go suede, or do you want to go leather? If leather, are you looking for more polished or more rugged? Then there’s the sole: stacked leather leans more formal, while crepe rubber keeps things casual and comfortable.
Most chukka boots you’ll find out there only have two pairs of eyelets (the rare pair will have three, but no more than that). So in terms of how to lace chukka boots, you’ve really only got one option and that’s a typical cross-laced pattern. Start by threading the lace into the bottom set of eyelets from the outside in, making sure you’ve got equal lace on each side. From there, cross the laces over each other and thread them through the next set of eyelets from the inside out. Tie them at the top and there you have it: a freshly laced pair of chukka boots. Easy, really.
As we mentioned, you don’t need to be any kind of styling expert to wear a pair of chukka boots and look great doing it. Just keep things generally casual — that is, don’t wear them with a tuxedo — and you won’t have any problems. That said, we’re here to help with a little styling inspiration.
One great way to rock a pair of chukka boots is with workwear-inspired clothing, calling to mind the boots’ military roots. So throw them on with your favorite denim jeans, a relaxed two-pocket button-up, and a tough all-weather jacket. The result: A look that’s equal parts stylish and ready for anything.
Todd Snyder English Waxed Dylan Jacket
Picture the classic American trucker jacket, but made from a British waxed canvas fabric from Millerain. Todd Snyder’s done just that, combining two iconic styles into one hearty autumn piece of outerwear.
Buck Mason Double Weave Vintage Two Pocket Shirt
Lightweight and breathable, this double-weave cotton shirt makes a great layer under any jacket. Not to mention the patch chest pockets double down on the workwear vibes of the outfit.
Mott & Bow Slim Warren Jeans
Cap off any casual outfit with some solid denim. Cut to a slim fit and made from a mid-weight Italian denim with a touch of elastane for comfort, these’ll be your new go-to jeans in no time.
If you’re looking to wear chukka boots to a slightly more dressed-up occasion — again, not formal by any means — it’s all about elevating the rest of the outfit. Try ‘em with a blazer and chinos, or a topcoat and a well-fitted sweater. Basically, anything that reads clean and smart should do the trick.
Sandro Long Coat Fastened with Three Buttons
Nothing more stylish to wear when the weather starts to cool down than a top coat. Sandro’s made this one nice and tailored to elevate any outfit you wear it with.
Banana Republic Italian Merino Turtleneck Sweater
If you don’t have a slim turtleneck sweater in your closet already, you should probably hop to it. This Banana Republic joint’s a classic, made from quality merino wool.
A.P.C. Navy Classic Cotton-Gabardine Chinos
Finish the look off with a handsome pair of chinos like these from A.P.C., a brand known for crafting the Platonic ideal of your favorite pieces of clothing.
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