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 year-round. That is, as long as you know how to wear them. It’s a lot to consider — but 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 their 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. With plenty of options to pick from leather to suede, make chukka boots the new favorite shoe in your wardrobe.
Why are they called 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. 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 Clarks after WWII, and it was based on the boots British soldiers wore in, you guessed it, the deserts of Africa.
Wearing chukka boots
How to pick a pair of chukka boots
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.
How to lace chukka boots
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.
How to style chukka boots
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.
Look #1: All workwear, no play
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.
Wrangler Western-Lined Canvas Jacket
Few brands embody stylish workwear the way Wrangler has for decades. Sure, you can look like you are one step away from a rodeo when all decked out in them, or you can don a canvas jacket like this and become the real-life Yellowstone character you have always wanted to be.
| Pros | Cons |
| Plenty of pockets for practicality | Can be constraining with a bulky sweater or top underneath |
| Quilted lining that helps keep warm without the weight | |
| Waxed cotton canvas ensures durability |
Snaps Clothing Rambler EZ Care Long Sleeve
Snaps Clothing’s Rambler EZ Care Long Sleeve is a simply crafted long-sleeve quality shirt that will last for years. Made with durable fabric and materials, this staple can easily be mixed and matched to create any look. Dress it up or dress it down, this long sleeve is certain to get plenty of use. Along with your boots, these two staples can easily form the base of any formal or casual outfit.
| Pros | Cons |
| Easy to reuse with other pieces | May require ironing |
| Variety of colors available |
Mott & Bow Slim Warren Jeans
Cap off any casual outfit with some solid denim. Cut to a slim fit and made from mid-weight Italian denim with a touch of elastane for comfort, these will be your new go-to jeans in no time.
| Pros | Cons |
| A staple for any season | Users report a tight fit |
| Added comfort and stretch |
Look #2: Down to business (casual)
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 them with a blazer and chinos, or a topcoat and a well-fitted sweater. Basically, anything that reads clean and smart should do the trick.
&Sons Boardwalk Peacoat
Military history is a common theme in the menswear world. Many of our favorite pieces can be traced back to their origins in the trenches, on the ships, or in the skies of our fearless ancestors. The peacoat is one of the best things (outside of freedom) that the Navy ever gave us, and this piece by &Sons is the cream of the crop of peacoats, and it’s the perfect coat to complement your military-inspired chukkas.
| Pros | Cons |
| Perfect for colder climates | Could be heavy for daily wear |
| Timeless style that will always be on trend | Fitted style can constrict movement underneath |
| Storm collar adds protection against nature |
Ralph Lauren Luxury Jersey Mockneck Pullover
There’s nothing quite like the look of a luxury mock neck to go along with a coat and boots. A classic pairing that works year after year, this combination is enough to become your new go-to outfit formula. Made with quality fabrics, this sweater option from Ralph Lauren gives you the perfect dose of sophistication that can elevate any of your outfits.
| Pros | Cons |
| Supersmooth jersey fabric make it easier to wear | Mock neck might feel constraining on some wearers |
| Variety of colors | |
| Classic design that won’t go out of style |
Brunello Cucinelli Slim-Fit Cotton-Gabardine Trousers
If anyone knows how to craft a quality product, it’s Brunello Cucinelli. In these Slim-Fit Cotton Gabardine Trousers, users can get the elegance and sophistication of trousers with a bit of a casual flair. Easy to combine with your chukka boots, these trousers are comfortable enough for daily errands, yet maintain enough style to complete any formal look.
| Pros | Cons |
| Can be worn on various occasions | Might be difficult to find the right length |
| Slim fit and crease give a sophisticated touch | The narrow leg can bunch with bulkier chukka boots |
Look #3: Suit up
Although most suit and tuxedo outfits are worn with classic dress shoes, chukka boots are the perfect footwear to give your look a distinct feel. Opt for sleek and similar-toned chukka boots that fit in with your suit without a hitch. Slimmer designs with leather materials work best in these situations, giving your suit the perfectly dressed style. Pairing your boots with suits isn’t an uncommon feat — it’s a chic go-to in colder weather, especially when visiting rougher terrain. Regardless, suits with boots are a good bet for anyone looking to add comfort and stability to their formalwear.
J.M Haggar 4-Way Stretch Dress Pants
A classic pair of suit pants like those from J.M. Haggar is a perfect way to easily blend your boots into your suit. While the bottom leaves room for your boots to move with ease, the slim fit still looks sophisticated and well tailored. Pair your suit pants with a matching jacket for a comfortable look that’s ideal for any formal event.
| Pros | Cons |
| Waistband additions allow for more comfort and ease | Some users report thinner fabric than desired |
Chukka boots FAQs
What is the purpose of chukka boots?
Chukka boots are a versatile type of footwear that you can wear for a variety of purposes and you can dress them up or down. Wear them for casual wear, business casual, smart casual, or for outdoor activities.
Are chukkas still in?
Yes, chukka boots are still in style. They have been a popular footwear choice for men for many years, and they continue to be popular today. There are several reasons why chukka boots are still in style:
- They’re versatile
- They’re comfortable
- They provide good support
- They’re stylish
Can I wear chukka boots with jeans?
Yes, as we’ve described above, chukka boots work perfectly with jeans. In fact, jeans are one of the most popular ways to wear chukka boots.
Here are some tips on how to wear chukka boots with jeans:
- Choose a pair of jeans that fit well. The jeans should be slim-fitting or tapered at the ankle, but not too tight.
- Cuff the jeans at the hem. This shows off the boots and creates a more polished look.
- Choose a pair of chukka boots that are the right color for your jeans. Dark wash jeans look best with dark brown or black chukka boots. Light-wash jeans look best with tan or suede chukka boots.
- Give your legs more room for your boots to move, bunched up jeans around the ankles aren’t a good look for anyone.
Here are some outfit ideas for wearing chukka boots with jeans:
- For a casual look, pair your dark wash jeans with a black T-shirt and brown leather chukka boots.
- For a more dressed-up look, pair some light-wash jeans with a white button-down shirt, navy blazer, and tan suede chukka boots.
- For a smart casual look, pair your dark-wash jeans with a gray sweater, navy chinos, and black leather chukka boots.
