These Men’s Boots Can Take You From the Office to the Trail (2024)

Hard to believe a pair with work boot roots that resembles a beefed-up Chelsea would be so ubiquitous, but there’s no denying the staying power of the Original 500 from Blundstone. Blundstone’s most popular boot toes the line between rugged and casual with a simple design and durable construction. Unlike other leather boots, there’s no break-in time and they’re remarkably comfortable from the first wear.

The leather uppers are water-resistant though some can seep in on the sides through the elastic gore. Pull tabs on both the front and back of the shoe make them easy to put on and kick off. The rubber outsole has great traction and gives you the sure-footedness you’d expect from your favorite pair of hiking boots with the comfort of sneakers.

You’ve probably heard some hype around Blundstones by now—they really are as good as people say. I’ve had a pair for six years, and if I had to break it down to cost-per-wear, I’d probably owe Blundstone some money. I’ve worn them hiking in Santa Fe, biking in the summer, and on nights out around town.

Key Specs

Chukka boots and Clarks are kind of like chicken sandwiches and Chik-Fil-A: the brand didn’t invent it, but they made the best one. The Desert boot by Clarks is the most recognizable chukka boot since it first debuted in 1950.

The soft leather uppers don’t need to be broken in on these boots, and they fold over for easy packing. The simple, two-eyelet lacing gives you a secure fit, but they’re easy to kick off and back on in a snap. The crepe sole—made of coagulated latex—is comfortable and pliable, but doesn’t offer a lot of traction, so I wouldn’t recommend wearing them on rainy days.

I have a pair that’s a half-size smaller than my typical size to account for the suede stretching over time, and after breaking in, they fit perfectly and I can wear them comfortably all day. I wear mine casually, and after nine years they’re still going strong.

I’ve only needed to replace the laces a couple of times and they’re beat up, but still wearable.

The Captain is a durable, versatile boot hits the perfect midpoint between a dress boot and a work boot. Flat waxed-cotton laces are durable but subdued for a clean look and speed hooks at the top allow for easy lacing. The leather uppers are flexible and require no break-in period so they’re comfortable form the first wear. The footbed has a cork construction that’ll form to your foot after time for more cushioning.

The stitched cap toe is dressy enough for daily use at the office and not look out of place on nights and weekends. The rubber sole is treaded and will grip slick streets but has a uniform color that looks more like stacked leather—a feature you typically see on dress boots—and can be resoled.

Key Specs

Eddie Bauer resurrected this design from 1964 and tricked it out with modern comfort. The full-grain leather uppers are waterproofed for protection against the elements and are more durable than a mesh fabric or nubuck leather. Its Vibram outsole has great grip that have seen me through slick city streets as well as smooth rock faces in the Catskills.

The plush insole and cushioned midsole make these some of the most comfortable boots I’ve tried. The shaft height is perfect for year-round wear since it offers a fair amount of ankle support without being too tall, which can be stifling in summer heat. It has a bit of a chunky silhouette but that, along with the D-ring lace system, adds to the old-school hiker aesthetic.

These have been in my personal rotation for the past year and completely replaced my sneakers in summer. Though it may be an unpopular opinion, I prefer something more substantial when walking and biking around the city. They’re sturdy without feeling heavy and chunky without being cumbersome.

Key Specs

Hoka is known for its ultra-cushioned running shoes, and its hiking boots deserve just as much praise. The Kaha 2 is a mid-top hiking boot that has a modern design and a lightweight construction. It has a high, plush footbed that’s supportive and provides all-day comfort whether you're on the trail or commuting in the city.

The waterproof nubuck leather uppers and Gore-Tex membrane ensure your feet stay dry no matter what weather you're out in. Five-millimeter lugs on the Vibram outsole provide great traction on any surface. Metal eyelets and speed hooks make them easy to lace up and take off, and won't rip or tear after heavy use. The padded tongue and ankle collar provide both cushion and stability.

They have a silhouette that’s similar to a hi-top sneaker so are great for those that don't want a traditional, leather boot. I use mine mostly for hiking or when I know I’ll have a long day on my feet because they’re so well-cushioned. Since these lean more hike/outdoor looks-wise, they may be harder to dress up.

Key Specs

The Moab 3 is a popular hiking boot that some like to use for casual, everyday wear for its comfort and waterproof capability. The uppers use a mix of leather and mesh that allow for some breathability. It has a roomy toe box so your toes won't feel cramped and won’t feel constricting after long periods of wear.

These look like hiking boots so they’re harder to wear into a formal office but they look fine with jeans and other more casual clothes. When comfort is at top of mind, a mid-weight waterproof hiking boot will cover a lot of your bases.

Key Specs

Red Wing is a well known name when it comes to work boots, but not all of us want safety toes or EH rating in our everyday footwear. The 6-inch moccasin toe was first introduced by the brand in 1952 and this is one of its most recognizable boots because of its construction, style, and also the slew of copycats since.

The full-grain leather uppers are water and stain resistant and the triple stitch construction bolsters durability. The brand uses hearty leather that's stiff and will require a couple weeks of wear before they’re comfortable, but that also means they’ll last.

Next to the moc-toe stitching, this boot gained popularity because of its outsole. The flat, traction tread—sometimes referred to as a wedge outsole—forms to your foot giving you some added comfort.

I’ve had a pair of mocs in the Oro Legacy for almost seven years and recently picked up this seasonal Alpine colorway—yes, I got the same boot twice. The two-tone stitching, black outsole, and matte olive uppers are interesting change-ups and I trust the brand’s commitment to construction.

The craftsmanship on a pair of Red Wings boots is on par with those that are nearing $1,000, and though they’re not cheap, you will undoubtedly get what you paid for.

Key Specs

The Bozeman will pull double-duty when as both a rain and winter boot because it’s both insulated and waterproof. The mix of rubber and neoprene on the uppers is flexible and give you mobility when out having to brave any rain or light snow—the seamless construction also bolsters weatherproofing to ensure your feet stay dry. It has a treaded rubber outsole for traction on wet streets and sidewalks.

Customers say these work well if you need a waterproof work boot and insist they keep warm in harsh winters. The pull-on design makes for easy on-and-off, and you can hose them down when they get dirty.

Key Specs

I’ve worn plenty of leather boots from rigid Red Wings to Alden boots, but these are my first pair of Western boots. I wanted to go all-out and try an exotic pair so went with the Ostrich leather. The material is soft to the touch, but doesn’t feel flimsy, and they’ve stretched comfortably at my instep.

I can walk around the city for a day without foot pain, but I don’t wear these in rain since the leather soles offer very little traction and can slip on slick surfaces like crosswalks and subway stairs. Ostrich leather is durable, but it’s also flexible and soft. It contains natural oils that help resist cracks or dryness, which is part of what makes the Wyatt cowboy boots so special.

They’re made from full-quill ostrich on the foot and calfskin for the shaft, with stylish designs throughout. The sleek round-toe shape distinguishes these from work boots that have a bulbous round or squared toe, and you can dress them up formally with a suit or trousers or wear them dressed down with a pair of jeans or cords.

These are snug and take time to break in, so you may struggle to take them off the first couple of wears. I went down a half size, as I do with all my boots, and the sizing was spot on—snug at first, then stretching and forming comfortably to my feet.

Cowboy boots may be a hard sell for some—especially Ostrich ones—but Tecovas makes a roper boot that’s more subdued.