15 Best Chukka Boots For Men

Posted in GEAR GUIDES, STYLE By

Having a dependable, reliable pair of shoes that you can reach for day-after-day can present a taxing search for the seasoned style vet or the beginning menswear aficionado alike. Some shoes — like a classic pair of sneakers — are only fit for the warmer months of spring and summer. Other — like durable winter boots — can be a bit too heavy for seasonal wear. But there’s one style that’s reliably classic and ready to stand up to everything from rugged denim and a henley to slim chinos, a blue Oxford and a navy knit tie. That would be the classic leather chukka boot.

It’s a style of ankle boot that’s not to be confused with the desert boot (which features a crepe sole), but chukka boots are every bit as wearable as any other pair of shoes in your closet. Even if you thought you had all your four-season footwear needs covered, there’s no telling how fair a dependable pair of chukka boots can take you, especially with their more casual open lacing and yet sturdy construction & dressy looks. Grab one or grab all 10 of the best men’s chukka boots below — they won’t let you down.

Taylor Stitch Chukka Boots

Taylor Stitch Chukka Boots

The best men’s chukka boots should grow with you, getting better with age and more stylish over time. That pursuit is helped if the chukka boots are pretty darn stylish out of the box to start — such is the case with the excellent Taylor Stitch Chukka Boots, made with beautiful weatherproof chocolate suede. These are sleek, stylish and surprisingly versatile — a stylish pair of men’s chukka boots can do all the heavy lifting in your outfit, without a doubt. So, keep it simple. Pair these with your favorite pair of broken-in blue denim and a chambray shirt, or wear ‘em with a tan herringbone suit this fall. – Shop Now

Frye Graham Brogue Chukka Boots

Frye Graham Brogue Chukka Boots

The great thing about a pair of chukka boots — particularly the best chukka boots for men as covered here — is that they can exist in two worlds at once. They can be edgy and rugged just as easily as they can be versatile and polished. Such is the case with the stellar Frye Graham Chukka Boots, featuring rich black leather and wingtip detailing. The black leather gives ‘em an air of rock n’roll cool — wear them to a rock show with slim blue denim and a chambray shirt after a casual day at the office. And the slim profile means that, yes, you can wear these to your next meeting when accessorized with slim tan chinos, a navy blazer and a white Oxford. – Shop Now

Timberland Wodehouse Lost History Chukka Boots

Timberland Wodehouse Lost History Chukka Boot

A slim profile, rich leather and a surprisingly dressy vibe doesn’t normally sound like Timberland, does it? And yet, the Wodehouse Lost HIstory Chukka Boots convey that vibe precisely, right up to the premium price point and premium construction. These are a surprisingly unique offering from the legendary brand, better known for its work boots than dressy chukka boots like these. Yet, that’s the beauty of the best chukka boots for men — they can be unexpected, surprisingly versatile and pleasingly rugged all at once. Wear these with dark denim and a grey crewneck sweater this fall. – Shop Now

Nisolo Emilio Chukka Boot

Nisolo Emilio Chukka Boot

Nisolo says that the Emilio Chukka Boots can take you from the boardroom to the bar, and we tend to agree. The rich Steel color is unique among chukka boots out there, and that’s but one o the fine qualities that make the Emilio Chukka Boots worthy of a spot on our list of the best chukka boots for men. The other defining factors? An agreeable price (under $200), durability and sustainable construction — pair them up with a leather Nisolo tote, classic cotton chinos and an olive pocket tee for reliable weekend style. – Shop Now

Astorflex Greenflex Desert Boot

Astorflex Greenflex Desert Boot

When the fine folks at Huckberry continue to vouch for a certain brand, we’re inclined to listen — and listen closely, at that. Such is the case with Astorflex, which makes a heck of a stylish pair of sustainable, comfortable chukka boots. Made with quality suede and eco-conscious materials, the Greenflex is as classic a pair of chukka boots as it gets, featuring a casual design, a comfortable rubber sole and our personal favorite, a rich Dark Khaki color. Looking for a pair of the best men’s chukka boots for early fall? You’re looking for these — step on into them. – Shop Now

Gordon Rush Desmond Chukka Boots

Gordon Rush Desmond Chukka Boots

Rich calfskin leather and a slim profile make the Desmond Chukka Boots from Gordon Rush perhaps the dressiest pair of chukka boots on this list. In our estimation, that means you can still wear ‘em with everything from navy chinos and a white Oxford to a thermal henley and rugged dark denim. They’re perfect for wearing into the fall and beyond, with sort of leather that’s only going to get better with age. When you’re searching for a shoe to fight the elements and look great alongside business casual looks aplenty, you’re going to want to consider the Desmond Chukka Boots. – Shop Now

Brooks Brothers Field Chukka Boots

Brooks Brothers Field Chukka Boots

You’ve surely shopped here for your classic Oxford shirt and your timeless navy blazer — now, consider looking toward Brooks Brothers to amp up your footwear situation, as well. The Field Chukka Boots feature the kind of classic looks you might expect from Brooks Brothers, including a slim profile and easy-to-style dark brown suede — in short, they’re the type of chukka boots that are going to work quite well with cotton Brooks Brothers chinos and a blue Oxford for Sunday brunch. Yet, they’ve also got a rugged outdoor vibe — keep ‘em handy to wear as an apres-ski shoe this winter at your cabin. Comfort, style and multi-season versatility? Sign us up. – Shop Now

UGG Dagman Chukka Boot

UGG Dagman Chukka Boot

Best known for cozy slippers and boots that your girlfriend or wife might love, the UGG Dagman Boot continues to represent the brand’s stylish push into the menswear arena — and that’s something we certainly appreciate. The Dagman Boots feature a soft lamb leather lining and rich suede for the type of style that works particularly well with essentials like a grey heather tee, an olive military jacket and light khaki chinos. A combo Treadlite and rubber outsole fuses durability and comfort for maximum longevity — when did you think you’d be able to say about UGG men’s boots? Best get to shopping. – Shop Now

Red Wing Heritage Weekender Chukka Boot in Copper

Red Wing Heritage Weekender Chukka Boot

As stunning as the Hawthorne Muleskinner iteration of this silhouette is, the Copper leather variety is something else entirely. They use that same water, stain and perspiration-resistant leather, and they do so in a unique silhouette that looks smart under jeans or chinos alike. The made-in-America construction absolutely makes them keepers, and there’s a good chance they’d look just as stylish with a casual suit as they would with a thick sweater and jeans. – Shop Now

Thursday Boots Brown Scout Chukkas

Thursday Boots Brown Scout Chukkas

Combine the looks of a premium dress boot on top — that’s thanks to the rich brown chrome leather — with the dependability of a durable rubber outsole, and you’ve got a pair of chukka boots that give you some major bang for their buck. At under $150, the Brown Scout Chukka Boot is sharp and almost effortlessly wearable year-round — it just looks that great, right down to the flat wax laces that provide some dressy appeal. The cut of this chukka boot is slightly higher on the ankle than other similar varieties, so it looks just as sharp with a tailored suit as it does with beat-up denim. – Shop Now

Johnston & Murphy Conard Cap Toe Chukka

Johnston & Murphy Conard Cap Toe Chukka

Super-clean stitching, a beautiful hand-burnished mahogany calfskin leather and an ultra-sleek silhouette make these a pair of chukka boots you can wear day after day after day. In addition to their outstanding look — which is again fit for wearing at the office with your best suit — they merge style with performance thanks to rubber sole and heel. That makes them ideal for trekking around the cobblestones of a major metropolitan city, and it also means they’ll fit right in during afternoon strolls for coffee in your hometown. Pair them up with olive chinos now, or rock them with grey wool trousers when snow starts to fall this winter. – Shop Now

Sperry for J. Crew Chukka Boots

Sperry for J.Crew Chukka Boots

Seeing as it’s still early in that transitional time between summer and fall, what better time to get ahead of the game when it comes to your fall boot shopping? That’s where Sperry and J.Crew — both experts in their respective fields — come into play. It’s fitting that the lauded American menswear retailer would team up with one of the country’s foremost heritage footwear producers for a pair of leather chukka boots that are going to fit right in alongside a chambray shirt and grey chinos just as well as they would with a pair of navy wool trousers later in the season. – Shop Now

Sebago Turner Waterproof Chukka Boots

Sebago Turner Waterproof Chukka Boots

Although originally known for its reputable boat shoes and other summer-friendly styles, Sebago also makes a chukka that’s durable, functional and stylish. The Turner Chukka (which looks especially sharp in a crisp black leather) is completely waterproof and ready for navigating slick city streets or country roads. The genuine leather welt pairs nicely with the slip-resistant rubber outsole for a pair of chukka boots that can take you from your commute to the office with no change of shoes needed. The dual cuff ankle also adds another durable touch and ensures a perfect fit, whether you pair these with rugged denim or slim dress trousers. – Shop Now

Hudson Shoes Lenin Brown Chukkas

Hudson Shoes Lenin Brown Chukkas

Rich brown leather and a sharp silhouette merge seamlessly to create a chukka boot that’s at once casual and refined. The hand-stamped leather is offset by a molded rubber inlay that gives these boots a dimension of durability one might not expect from a chukka boot. The contrasting boot tab is handy for slipping these shoes on and off on the go, and if you’re wearing them, it’s safe to assume you want to get where you’re going in versatile style. After all, these boots can take you from the office to dinner and a show in quick order. And then, they can do it all over the next day. – Shop Now

Trask Brady Chukka Boots

Trask Brady Chukka Boots

If you want a pair of chukka boots crafted to last year after year, there’s one type of leather you want to look for, and that would be Horween. Saddle tan American bison leather makes these chukka boots one-of-a-kind, as does the Ortholite cushioned insole and a sturdy Vibram outsole (the best in the business). Stitchout construction allows for greater flexibility and ease of movement, resulting in a pair of chukka boots that’s durable, stylish and supremely comfortable. Like the other great chukka boots on this list, this pair will work right now with a khaki chino suit, and it’ll work in the fall with a thick cardigan and jeans. – Shop Now

Best Men's Chukka Boots

Related

Editor's Picks



Get the Collection

Gear for Men. Straight to your inbox every Tuesday.

Everyday Carry

Everyday Carry

The essentials.


Koenigsegg Naked Carbon Regera

Koenigsegg Naked Carbon Regera

Attention to detail.


Abita Office Party

Abita Office Party

A limited-release holiday brew.


Flint and Tinder Waxed Ridge Parka

Flint and Tinder Waxed Ridge Parka

Protection from the elements.




All Posts