The Best Chukka Boots For Effortlessly Versatile Spring Style

Lace up a pair of these stylish kicks.

The classics in the menswear world tend to have their own way of circling back around each year, without fail. Reliability and a certain “cool” factor tend to come mind, especially with, say, some of the best chukka boots for men. The trusty ankle boot, prized by soldiers in the dusty desert, morphed into a prep staple and then an edgy, endlessly rugged pick.

There are guys like Steve McQueen (back in the day) and Daniel Craig (in modern times), not to mention well-heeled world travelers like Anthony Bourdain to thank for its place in the modern pantheon. But again, some things tend to never quite go away, and stylish chukka boots (in rich suede or handsome leather) fit the bill nicely. These are the pairs to lace up this spring.

Clarks Desert Boot in Sand Suede

Let’s get one thing straight: If, like we said, the classics never really die, then Clarks might have the most enduring legacy of all in the world of stylish ankle boots. Whether in this seasonally friendly suede or rich beeswax leather, every detail is casually cool and perfect, from the crepe outsole to the two-eyelet construction and breezy silhouette. $150

Todd Snyder Nomad Boots in Olive

Just about two years ago, famed American menswear designer Todd Snyder debuted his first-ever shoe, the Nomad Boot. And in the seasons since, he refreshes his own take on the classic desert boot in intriguing colors, including this handsome Olive number. It rests atop an Italian rubber sole with timeless two-eyelet construction, all the better to wear with light wash or natural-toned jeans. $278

Astorflex Brownflex Chukka Boots

Where can you find a versatile pair of Italian-made chukka boots for a price tag that tops nearly every other designer brand? At Huckberry, and the details are expertly crafted in this retailer-exclusive pair, from the natural crepe rubber sole to the soft European suede upper. $215

R.M. Williams Kingscliff Suede Chukka Boots

R.M. Williams, out of Australia, makes some of the toughest boots for hard living and working Down Under, but its Kingscliff Suede Chukka Boots are a touch more refined and sleek. The rubber outsole remains the same for long-lasting seasonal durability, while the profile can be dressed up with a linen suit or dressed down with dark blue jeans. $510

Allen Edmonds Chandler Chukka Boots

Not every pair of chukka boots needs to be constructed from supple suede, although it’s a wise bet to keep a pair or two (or three) handy. Allen Edmonds uses antique hickory leather with tons of depth, the kind that develops a visually pleasing patina over time. Wear these to the office with tobacco-hued chinos or with light wash jeans and a rugged henley. $379

Tod’s Desert Chukka Boots

If you find yourself reaching for boots more often than dress shoes, even in tailored situations, these elegant Tod’s chukka boots in crisp black leather might be a wise move. As ready to pair with a navy tropical wool suit as a khaki cotton suit, they seem like just the kind of chukka boots that James Bond might approve of. $447

Magnanni Maren Chukka Boots

Magnannini crafts its shoes with distinctly bold silhouettes and toe shapes, the sort of looks that wear well from the coast of Italy to the foggy streets of London. Add in some textured leather, as with these sleek three-eyelet chukka boots, and you’ve found a winning pair at an accessible price. $297.50

Gordon Rush Austin Chukka Boots

Look to Gordon Rush for striking the right balance between tasteful dress footwear and comfort, as the Ortholite insoles of this pair prove handily. The dark brown leather isn’t a half-bad option either, particularly when it comes to styling with olive chinos or even selvedge denim. $265