This guide to the best boots for men covers nine different categories, including work boots, Chelseas, chukkas and more.

Boots always seem to get more done than shoes. While shoes are busy arguing semantics in a boardroom, boots are out in the garage welding shit. Shoes spend their weekend shanking golf balls while boots are going over, around and through every surface on earth. Truth is, shoes were for buzz-cut boys playing acoustic guitar until boots came over from England and started a revolution. Boots have long belonged to the movers and shakers of history, and dammit if they’re not going to keep going. Here are the 50 best pairs you can buy right now.

Additional contribution by Matthew Ankeny.

The Chelsea Boot

Chelsea boots began life in England in the mid-19th century and didn’t stray far from home until recently. The elasticized wonders were a staple of the mid-’60s mod scene and protected the feet of seemingly every British invader from John to Ringo. Recently they’ve seen a revival on many of menswear’s best dressed. The silhouette is very slim and features elastic side panels and heel pull-tabs.

Declan Chelsea Boot by Grenson $285

Chatsworth Suede Chelsea Boots by Loake 1880 $318

Suede Chelsea Boot by R.M. Williams $495

Suede Chelsea Boots by Common Projects $525

Polished Leather Chelsea Boots by Saint Laurent $855+

Lawry Suede Chelsea boots by John Lobb $1,870

The Ankle Boot

Boasting a higher degree-of-difficulty than the Chelsea boot, ankle boots might be the coolest footwear ever made. They’ve graced the feet of rock stars, played their fair part in creating a few illegitimate children and complimented the tightest pants mankind has had to offer for decades. The silhouette is similar to the Chelsea boot, but the Ankle boot utilizes zippers or straps to secure instead of stretch-panels.

Chris Inside Zip Boot by Frye $229

Suede Jodhpur Boots by AMI $550

Julian Suede Jodhpur Boots by Acne Studios $445

Jonah Boots by Lucchese $795

Suede Jodhpur Boots by Saint Laurent $1,045

The Wingtip Boot

You got formal embellishment on my casual footwear! You got casual footwear on my formal embellishment! The wingtip is dressed up enough to be worn with a suit and casual enough to end up under denim or a pair of cords. Wingtip broguing brings a aire of formality to this style of lace-up boots.

Dalton Wingtip Boot by Allen Edmonds $445

Fred Brogue Boots by Grenson $365

Caldecott Boots by Church’s $479

Stow Brogue Boots by Tricker’s $480

Leather Wingtip Brogue Boot by Thom Browne $1,290

The Chukka Boot

About as casual as all-leather boots get, the chukka (or desert) boot was first worn by British soldiers in Africa during WWII. Afterward, they made their way across the Atlantic, becoming a casual staple for the second half of the 20th century and still gracing the feet of stylish men in the cooler months. Clarks made the originals, but upmarket offerings only improved on the formula. They lace-up just above the ankle and traditionally feature a soft crepe sole.

Desert Boot by Clarks $79

Classic Boot by Wild Bunch $225

Scout Boot — Coyote Sumner by Maine Mountain Moccasin $325

Hand-Sewn Desert Boot by Feit $300

Suede Desert Boots by Connolly $800

Grove Suede Chukka Boots by John Lobb $1,465

The Hiking Boot

We’ve kept a respectable distance from some of the technical boots, but the best pairs of old-school hiking boots boast the same alpine prowess that made them popular in the first place along with a great look. Sturdy soles, heel support and lace-to-toe closure typify the style.

Ripple Sole Scarponcino Boot by Fracap $249

Danner Light by Danner $380

Tofane NW FTX RR Boot by Zamberlan $470

Jura Boots by A.P.C. $272

Suede Hiking Boots by Viberg $710

The Hunting Boot

For actual hunting you may want something more technically advanced, but the hunting boot is a staple in the Northeast and has ensconced the feet of everyone from Hemingway to Thad in Sigma Chi. They may not be as warm or as waterproof as some others, but Ernest would probably tell you to sack up. The traditional style features a hand-sewn moc-toe, a lace-up closure and a durable grippy outsole.

The Original Duck Boot by L.L. Bean $114

Dresden boot by Rancourt and Co. $225

American Bison 5.5 “PH” by Russell Moccasin Co. $438

Mohawk Trail Boot Crepe by Maine Mountain Moccasin $399

Angler Boots with Cortina Sole by Yuketen $409

The Work Boot

Strong, long-lasting and just stylish enough to stay on your feet for most of the colder months: that’s all a work boot really needs to be. Little wonder that the design was more or less perfected half a century ago. The no-frills lace-up style protects the lower legs and feet and usually features a durable lug sole.


Apache Steel-Toe Logger by Chippewa $215

Blacksmith Oil Tanned Boot by Red Wing Heritage $300

Evans Boots by Wolverine $400

BuilderPro by Nicks Handmade Boots $429

NFPA Smokejumper by White’s Boots $500

Zermatt Suede Boots by Visvim $895

The Trench Boot

Worn since WWI, the trench (sometimes called army or officer) boot is a handsome staple that’s shaken its military roots and manages to look a bit more cleaned up these days than it did stomping into Flanders. Similar to the work-boot, this silhouette has a lower profile that is easier to incorporate into a variety of wardrobes.

Kenton Plain-Toe Boots by J.Crew $248

Brown Trench boot by Oak Street Bootmakers $426

Front Range Boot by Truman Boot Company $580

Service Boot by Viberg $670

Indy Boot by Alden $563

Combat Boots by John Lofgren $820

The Cowboy Boot

Like many Americana wardrobe staples, cowboy boots are rooted in function. Pull them on, wear them hard and use them for years. There are two mains styles: traditional cowboy boots that feature a riding heel (taller and angled) and roper boots that have a shorter heel, designed to handle a day of walking. The pointed toe and tall shaft make this boot instantly recognizable.


Cowboy Boots by Dan Post $159

The Cartwright by Tecovas $235

Pecos by Red Wing Heritage $320

Ranch Hand by Heritage Boot Co. $420

Chocolate Rista Calf by Tony Lama $309

Bannock by Lucchese $595