Of all the menswear must-haves a great wardrobe should contain, is there anything more essential than starting from the ground up with a pair of chukka boots? In between the sturdy lace-up work boot and the subtle dress shoe sits the perfectly rugged-yet-refined, endlessly versatile ankle boot design of the chukka boot.
In fact, on any given day, there’s a very good chance I’m wearing a pair of leather lace-up boots with a two or three-eyelet design. The ankle boot look works well with chinos, with faded blue jeans, dressy wool pants, or with seasonally friendly corduroy or linen pants, and in just about any style situation short of black tie. Consider the chukka boot your new best friend in the world of stylish men’s boots, as I do.
If you don’t have a set of timeless Clarks boots in your footwear rotation, this iconic pair is a great place to start.
I’ve found that over the years, I keep coming back to Clarks boots – fairly priced, nicely made, available in a range of colors and styles. In fact, this chukka boot is one of my go-to pairs of boots to wear with jeans (particularly classic dark blue jeans in a slim-straight cut).
The design is simple, subtle and endlessly versatile, especially in rich Beeswax that gets better the more you wear them and break them in. You might say they’re the boot upon which all other pairs of chukka boots are based on, and you wouldn’t be far from the truth.
Although seemingly simple on the surface, the chukka boot can be switched up in some surprising ways. Take the Tyler Chukka from Rhodes Footwear.
The in-house Huckberry brand makes a streamlined pair of dress boots as well as rugged moc toe work boots – here, they’ve taken a similar work boot wedge sole and morphed it into an effortlessly cool chukka boot style.
That’s not the only thing to love, because the waxy tumbled leather develops its own character the more you wear ‘em, too.
Suede can be a notoriously difficult material to care for, even when it comes to the best chukka boots for men, so it’s refreshing to see a brand like Taylor Stitch take things up a notch.
Here, they’ve used a lightweight-yet-hardy mushroom suede, then worked with artisans in the footwear hub of Leon, Mexico to get the construction just right.
These boots also hit higher on the ankle, for a more secure fit. And moc toe construction adds a touch of style and more reinforcement for years and years of wear alongside your essential Taylor Stitch chinos.
It’s like I’ve said before here at WERD: Chukka boots aren’t always the most dressy style, but if you’re on the hunt for chukka boots you can wear with, say, a navy suit, then the Laval Chukka Boots are as solid an option as it gets.
The key is handsome full-grain leather with just enough of a sheen that they’ll buff up nicely. The toe box is still nicely rounded though, so this made-to-order pair of boots is certainly versatile enough to wear with your trusty blue jeans. These are designer quality without the hefty price tag, at least in my book.
You’re probably familiar with Red Wing’s legendary Iron Ranger Boot, a tough-as-nails lace-up boot made for braving the elements. I myself find my Red Wing Iron Ranger Boots getting tons of wear these days, but the Weekender Chukka is just as covetable and every bit as worthy of your wardrobe.
It’s got all the trappings of a work boot, with a weather-resistant leather upper and a spring ComfortForce footbed. Plus, this pair of classic chukka boots is USA-made in much the same way as Red Wing Heritage has been doing things for years – talk about boots you can feel great about buying.
Not every situation is going to call for the weather-ready, work site and downtown-approved Timberland Six-Inch Boot in a crisp Nubuck leather.
Timberland swerves from its classics with this sneakerboot-style chukka, boasting a rugged brown leather upper (it’s waterproof, fear not), along with a sustainable faux-fur lining for warmth.
The fact that the lining is made from material developed from recycled plastic bottles is a nice touch, and the OrthoLite footbed is an A-plus feature in terms of day-to-night comfort.
Grenson is still fiercely committed to old-school production methods, which lifts them above other footwear makers – and the company also has long-standing roots as a pioneer in the British footwear space.
It all makes for an exceptional pair of chukka boots, made with Goodyear welted construction in a resoleable design.
Contrast stitching plays nicely off the elegant upper, while rubber pods on the leather sole deliver crucial grip on cobblestone streets. To London and beyond with your new favorite chukka boots.
The casual ankle boot design of the chukka boot isn’t all that different from some high-top sneakers, at least when designed by SeaVees, a brand that epitomizes California cool.
When the company’s famed, low-profile canvas sneakers aren’t quite cutting it, opt for the SunTans Chukka.
The soft, supple suede is set atop a natural and recycled rubber outsole for spongy support and some literal spring in your step. The design itself seems tailor-made for wearing with rolled, faded blue jeans and one of the best men’s hoodies for easygoing style.
Thursday Boots started with a few classic, well-made designs that quickly became a major hit, including the Scout Boots.
Years ago, the Scout Boots were one of the first pairs of chukka boots I ever tried, and I was instantly hooked on the style.
The profile on these boots is refined and streamlined, yet they’re built with a sturdy, grippy lug rubber sole for good measure. I personally appreciate that studded lug rubber sole for added traction, as opposed to some boots made with a soft, springy yet not-as-grippy crepe rubber sole (the kind you’ll find on Clarks chukka boots).
The maker of some of the best men’s dress shoes also just so happens to make some of the best men’s chukka boots.
Care and craftsmanship sit comfortably at the forefront of the famed U.S. footwear maker’s focus – these boots are handmade in Wisconsin and feature a sturdy, slightly taller three-eyelet design. Best of all might be the rich Loden Suede, which shakes up colors in your footwear rotation quite nicely.
The chukka boot as made by a brand like Clarks is oft-imitated, never quite duplicated, but the family-owned factory purveyors at Astorflex are offering up a nice alternative.
Set on a similar natural rubber sole to the timeless Clarks boots, these feature aged nubuck leather that rests atop the company’s custom footwear last.
There are also pairs made with suede for an even more casual change of pace. Plus, the company’s footwear shape is casually rugged, while the leather upper will only get better with age.
For as much as the chukka boot was a style pioneered by British brands like Clarks, FRYE has done a standout job at bringing plenty of casually rugged boots to the masses here in the States.
The famed Northeast footwear maker crafts its chukka boots with a touch of modern edge (to go along with time-honored production methods). That means using Goodyear welt construction for durability, while at the same time using a variety of vintage-style and finely aged leathers for a worn-in look out of the box.
It’s been worn in some iterations by soldiers in the dusty desert (hence the “desert boot” tag) but quickly become a go-between for stylish gentlemen who want the coverage of an ankle boot with a more streamlined design. The original desert boot was brought to the masses by Clarks (we’ll get to those in a moment), and plenty of companies have tried their hand at the two or three-eyelet ankle boot design.
The style works well with tailored chinos or fall-friendly corduroy pants, but it also wears comfortably with your favorite pair of broken-in jeans. Believe it or not, you can team the right pair – a pair made with, say, sleek and shiny black leather – with your best wool or cotton suit.
I personally prefer a pair made with a soft, supple full-grain leather, as opposed to suede, but pairs from companies like Clarks are timeless and come in a variety of materials and colors.
When wearing my chukka boots, I match the leather or suede material accordingly with my pants. In the depths of fall, I’m often wearing dark brown leather or whiskey-toned leather chukka boots with dark blue jeans or even tobacco-hued chinos. In the spring and summer, my light or dark tan suede chukka boots wear well with light wash jeans or olive chinos (to name but two examples).
You can now find chukka boots in shades of brown, black, tan or olive – to name but a few – sometimes designed to rest atop a springy crepe rubber sole and other times, sitting atop a sturdy lug rubber outsole.
Even James Bond wears chukka boots now (just look closely at scenes going back to Quantum of Solace).
If there were a boot that every guy can wear, it’d be the chukka boot.