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 long gone, fall just left, we’ve now reached the season where a solid boot is all you really need to cover you everywhere from the workplace to your weekend getaway.
That’s where a dress boot comes in. Originating in Victorian England when the Royals requested a shoe that would be as suited to horse riding as everyday living, 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 winter for years to come. Here’s where to start.
The Best Men’s Dress Boots, According to GQ
Thom Browne Classic Wingtip Lace-Up Boots
READ MORE
Our Legacy Camion Boots
READ MORE
Meermin 514491 Black Calf and Softcalf Boot
READ MORE
Beckett Simonon Oscar Boots
READ MORE
Best Slip-On Dress Boots: R.M. Williams Comfort Craftsman Chelsea Boots
R.M. Williams
Comfort Craftsman Chelsea Boots
Pros
- Shockingly comfortable rubber sole means no blisters, scabs, or break-in period
- Perfectly chiseled profile looks killer with literally every pant we’ve worn ’em with
- Premium Australian craftsmanship
- Unimpeachable outback pedigree
Cons
Chelsea boots—especially the lighter-colored variety—caught some strays in recent years. But that fickle talk does a disservice to what should be the 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: Thom Browne Classic Wingtip Lace-Up Boots
Thom Browne
Classic Wingtip Lace-Up Boots
Pros
- Made it Italy
- Calfskin leather
- An archive-worthy designer piece
Cons
Tread confidently in these brogued-out (is that a phrase?) wingtip boots from Thom Browne. Not only are they a subtle way to flex your appreciation for the occasionally out-there designer, but they’re also made in Italy from only the best calfskin leather. 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
Pros
- Near-indestructible Vibram role
- Sleek, supple calfskin leather
- Premium Portuguese craftsmanship
- No shortage of cool-guy credibility
Cons
- Silhouette is deceptively versatile, but skews casual
- Gently-squared toe is great if you work at GQ, but might elicit a few sideways glances at your law firm
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: Meermin 514491 Black Calf and Softcalf Boot
Meermin
514491 Black Calf and Softcalf Boot
Pros
- Sheepskin lined
- Under $300
- Flex Goodyear Welt
Cons
- Not many! Perhaps the sole could have a little more tread
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. Meermin’s version packs details like heavy-duty hardware, a sheepskin lining, and a (more comfortable) flex Goodyear Welt sole into a sub-$300 package built for urban commuting. 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 suit) or down (think vintage Carhartts) to your liking. What’s more, that soft calf leather adds a bit of relaxed spice without committing you to full brogue.
Best Budget Dress Boots: Beckett Simonon Oscar Boots
Beckett Simonon
Oscar Boots
Pros
- Moisture-absorbing Vachetta leather lining; abrasion-resistant SBR heel caps
- Supple full-grain leather; steel shank-supported outsoles for added balance
- Phenomenal value
- Top-notch customer service the whole way through
Cons
- Made to order, so wait times can run long
Boot shopping, as we’ve admittedly shown, can get expensive quickly. If you’re looking for a pair of dress boots that are even more affordable, but still have more shine than a Blundstone, 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
Pros
- Easy-access zipper
- Goodyear-welted construction; premium goat leather
- Phenomenal value
- Real-deal rancher bona fides
Cons
- Sizing can be a puzzle
- Silhouette is deceptively versatile, but skews casual
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 its 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.