The Best Dress Boots for Men Are Seriously Stylish Stompers

Do you hear that? It’s the faint sound of dried leaves crunching under a pair of the best dress boots for men. Summer is over; we’re now entering the the season where a solid boot is all you really need to cover you everywhere from the workplace to your weekend getaway.

Dress boots originated in Victorian England when the Royals requested a shoe that would be as suited to horse riding as everyday living. But over the years, the silhouette, especially the Chelsea boot, became a central part of the rock-god wardrobe, landing on the feet of The Beatles, the Rolling Stones, and, eventually, average dudes simply trying to dress the part. Today, it has settled somewhere in the middle—a versatile, three-season essential that offers stability and style in equal measure.

If you haven’t broken in a pair of your own yet, don’t worry: the best dress boots for men qualify as what your grandpa might call “shit-kicking shoes”—meaning they can more than withstand whatever the weather throws at them—without sacrificing form for function. Buy the right version, and you’re left with one less decision to make every fall for years to come. Here’s where to start.

The Best Men’s Dress Boots, According to GQ

Best Slip-On Dress Boots: R.M. Williams Comfort Craftsman Chelsea Boots

Chelsea boots—especially the lighter-colored variety—have gotten a bit of a bad rap in recent years. But that fickle talk does a disservice to a true workhorse of your footwear rotation. Regardless of trend cycles, the Chelsea boot will always be a staple, because of how easy it is to slip-on, and how good it looks with jeans and dress pants alike. And few make a better-looking, longer-lasting pair than Australia’s R.M. Williams. Crafted from a single piece of leather (to truly keep out the elements), and with a a comfort sole reminiscent of some sneakers, there’s a reason R.M. is able to keep multiple storefronts open around the world, and a reason that said stores are always full of men buying their first, second, or even fifth pairs.

Best Wingtip Dress Boots: Tricker’s Stow Boots

Tread confidently in these brogued-out (is that a phrase?) wingtip boots from the master British shoemakers at Tricker’s, who have been lacing gentlemen’s feet since 1829, and remain family-owned to this day. Especially popular in Japan, the Stow boot is one of the company’s best-sellers—watertight and made from tough (but light) calf leather, its distinctive brogue detailing softens that rugged construction just enough. Pair these boots with a dark, wool suit and a turtle neck, or more casually, with a wider chino pant and a crisp, tucked-in T-shirt. To be honest, any slightly muted fit will balance what could be considered one of the louder styles of boot on this list.

Best Dress Boots for Fashion Guys: Our Legacy Camion Boots

You’re unlikely to go astray buying anything from Our Legacy. The iconic Swedish design label remains one of the few able to stay atop the menswear zeitgeist through up and down trend cycles and multiple economic crises, and part of that resilience is down to the year-in, year-out success of the Camion Boot. The hyper minimal style still packs a few subtle design details, like chrome logo hardware and a beefy, no-slip Vibram sole, while the silhouette is instantly recognizable for all the right reasons. Pair them with faded, slim-straight denim for a nonchalant look.

Best Cap-Toe Dress Boots: George Cleverley Cap-Toe Pebble-Grain Leather Boots

The cap-toe shoe is one of the most classic and iconic constructions in formal menswear, and its application in boots created one of the cleanest silhouettes you can possibly add to your footwear collection. George Cleverley—a British shoemaker that’s earned a Royal Warrant for its abilities—makes the best there is, and will also repair it for you, if needed, over the course of your lifetime. Like most of this list, they’ll look best in black or brown with a not-too-skinny pant, and can be dressed up (with a navy suit) or down (think vintage Carhartts) to your liking. What’s more, that pebble-grain leather adds a bit of relaxed spice without committing you to full brogue.

Best Budget Dress Boots: Beckett Simonon Oscar Boots

Boot shopping, as we’ve admittedly shown, can get expensive quickly. If you’re looking for dress boots under three bills, it’s hard to pass up these beauties from modern consumer-focused footwear startup Becket Simonon. Waxed cotton laces and a soft Vachetta leather lining make these true all-arounders for fields or the city; heck, if you wear ’em with the right pants, people might just think you’re wearing the Our Legacy joints above.

Best Dress Boots for Cowboys: Tecovas Dean Boots

The urban cowboy trend may be sunsetting a bit (or rounding into a subtler, more workmanlike Springsteen aesthetic?) but a classic western-style boot will never be out of fashion, even if you’ve never seen an episode of Yellowstone. Helpfully, Tecovas says their 8-inch Dean boot is ‘slim-jean’ compatible—perfect to match with Wrangler’s also always-in-style cowboy cut jeans. We like it’s sturdy 1.5-inch heel (who doesn’t like being taller), and how they give a nod to the Western look, without presenting like you just came from a costume party.

Best Dress Boots for the Slopes: Morjas Hiking Boots

The classic, evocative mountain boot silhouette conjures images of alpine treks (or, let’s face it, upstate leaf-peeping) in the minds of fashion boys and hikers alike. Brands like Danner made their name with such heavy duty, outdoor-centric boots, but the price was always as high as the quality. For slightly less cash, but just as much style, it’s hard to find a finer boot in this mold than these, from Swedish brand Morjas. If there’s one boot on this list that I’m 100% certain can handle the worst of winter weather it’s these, even if the only hike you’re taking is from the front door to your Uber.

More Dress Boots We Love

Another Great Slip-On Option: Celine Leather Chelsea Boots

Another Great Wingtip Option: Thom Browne Classic Wingtip Lace-Up Boots

Another Great Fashion-Guy Option: Hereu Quadra Grainy Boots

Another Great Cap-Toe Option: Allen Edmonds Park Cap-Toe Boots

Another Great Budget Option: Solovair 6-Eye Derby Boots

Another Great Cowboy Option: Rhodes Roper Zip Boot

Another Great Slopes-Ready Option: Meermin Hiking Boots