Best Men's Chukka Boots

10 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.

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. – $149

Red Wing Heritage Weekender Chukka

Red Wing Heritage Weekender Chukka

Red Wing’s history of quality and longevity speaks for itself, so it’s only fitting that the brand’s new Weekender Chukka hardly needs an introduction. It’s crafted from the brand’s remarkably durable S.B. Foot Tanning Company leather with the brand’s ComfortForce foot. The stitchdown construction means it’s extra sturdy, and the leather itself is water, stain and perspiration-resistant. How many other chukka boots can claim that? The unique silhouette makes it an easy go-between from lightwash jeans in the summer to wool cargo trousers in the fall and winter. It’s the perfect blend of casual style and heritage construction, and not that many chukka boots can claim such a balance. – $230

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. – $175

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. – $125

Blu Kicks Tahoe Sand Chukka

Blu Kicks Tahoe Sand Chukka

A lightweight beige chukka is an underrated style weapon. Earth tones are surprisingly versatile in color and help offset either dark or light wash denim, and the agreeable price and eye-catching brick red sole of this pair makes them perfect for the final days of summer (and beyond. They’re handmade in Mexico from premium materials and feature a leather lining for plenty of comfort. These are the type of chukka boots you can wear with rolled navy chinos and no-show socks for a slightly bold, style-forward move. You could also team them up with rugged dark blue denim and your favorite pocket tee on the weekends. – $128

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. – $135

SeaVees 3-Eye Chukka Boots

SeaVees 3-Eye Chukka Boots

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. – $178

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. – $225

Red Wing Heritage Weekender Chukka Boot in Copper

Red Wing Heritage Weekender Chukka Boot in Copper

As stunning as the Hawthorne Muleskinner iteration of this silhouette is, the Copper leather variety is something else entirely. It’s fitting that these are sold via lauded menswear designer Todd Snyder’s Web site, as he’s made a career out of designing heritage-inspired staples that you can (and should) wear just about anywhere. 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. – $230

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. – $265

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