In 2021, figuring out where the best dress shoes for men fit into your footwear rotation is more confusing than ever. Your friends swear by Adidas. Your coworkers refuse to take off their Allbirds. And everybody is wearing Crocs. (Crocs!) Finding room in your heart, let alone in your closet, for shoes you once associated with the drudgery of your 9 to 5 is a tough ask.
But here’s the thing: the most compelling dress shoes on the market today don’t feel the same as their predecessors. The craftsmanship is still there, sure, but the fussiness? Not so much. That’s why skipping over reams of other footwear options and actively choosing to wear a dress shoe right now feels almost rebellious. Dress shoes will always be a stalwart of the work wardrobe, and a go-to for more formal occasions. But in their Platonic form they can also be surprisingly hip. Sexy, even.
Which brings us to our next point of business: What is a dress shoe in 2021? Derbies definitely fit the bill. But do Chelsea boots? How about loafers? The answer, in a word: yes. All those will do if the place you’re headed skews lax on convention. But sometimes circumstances call for a more traditional silhouette, and when they do you’ll be glad you turned here.
And yet! In opting for a pair of dress shoes, you’re making a conscious decision to eschew all the furry clogs, freaky sneakers, and (gulp) cool-guy FiveFingers out there, true—but that doesn’t mean you need to stick exclusively to the usual suspects. Many of the options we gathered here—the absolute best dress shoes for men, thank you very much—will sync up well with the trappings of standard business casual attire, but they’ll also look at home elevating your biggest weekend fits. Which means whether you’re wearing them to your first in-person meeting in two years or your first in-person date in nearly as long, they won’t steer you wrong. Going with the (pebble) grain never looked so good.
The Best Plain-Toe Dress Shoes
First things first: if you’re in the market for a dependable pair of dress shoes—the type you won’t have to chuck after a year and change of hard wear—it’s going to cost you. But if you’re willing to cough up the dough now, the investment will pay dividends down the line. Every pair of shoes here could be the last one of its kind you’ll ever have to buy. (Assuming, of course, you have the appropriate self-restraint.) And that’s doubly-true when it comes to Alden’s plain toe blucher, a legendary silhouette rendered in the New England shoemaker’s Horween shell cordovan. Alden’s been around since the late 1800s, and making shoes like these—supremely durable, surprisingly versatile—ever since. The blucher is the brand’s signature style, and it’ll look just as good with a tweedy sportcoat and faded jeans as it will a hefty cable-knit and slouchy dress pants.
If the Aldens are a little outside your price-range, Frye’s plain-toe oxfords are a stellar substitute—especially when they’re on sale for over $100 off. Another bang-up option: Beckett Simonon’s whole-cut dress shoes, crafted from a single piece of leather, a process that normally costs five times what they’re charging.
The Best Cap-Toe Dress Shoes
Need a pair of dress shoes you can wear to a wedding, funeral, job interview, or court appearance? (No judgement here, pal!) A black cap-toe is a surefire bet. The jack-of-all-trades style is one you can always turn to with confidence, secure in the knowledge that wherever you go you won’t be in gross violation of some obscure, socially-mandated dress code. There’s a lot of options out there, but George Cleverly’s are in a league of their own. Cut by hand in England and detailed with the subtlest hint of broguing along the seams, they’re wholly impervious to fashion’s fickle whims and all the better for it. Get married in ’em if you choose—heck, get buried in ’em, too. But get a pair you should.
No, a leather lace-up will never be as comfortable as a running shoe. But if cushioning is a primary concern, Allen Edmonds’ signature insoles will get you pretty damn close. Not sure you want to pony up the big bucks on a dress shoe? Johnston & Murphy makes a classic cap toe for below two Benjamins.
The Best Brogue Dress Shoes
The brogue takes its name from the the distinctive perforations (or “broguing”) found on the toe and outer edges of the style. And like so many of its pedigreed footwear peers, Trickers makes an absolutely killer pair. The British brand specializes in refined dress shoes that are far from precious, often built on top of ultra-sturdy Dainite soles you could hoof around in for years before they show any sign of damage. In a shade of rich, chocolate-y suede, its Bourton derby is specifically designed to take your navy suit from soulless corporate uniform to the stuff of street style fodder in a matter of seconds. You can wear these puppies with a full tailored rig, sure, but few shoes will look better paired with a gun check blazer, cashmere turtleneck, and dark indigo denim—along with pretty much everything else in your closet.
Nearly every cordwainer worth naming makes a solid brogue, which means it’s easier than ever to find one that won’t break the bank. Dr. Martens is always a safe bet, but if you’re looking for an option with a dinner party-worthy backstory, Thistle Shoes makes brogues inspired by traditional Scottish footwear and reinforced with steel quarter tips and all-terrain rubber soles, the dress shoe equivalent of four-wheel drive.
The Best Wingtip Dress Shoes
The wingtip, named for the wing-shaped broguing that typically extends from the silhouette’s toe cap to its heel, is the Lexus of dress shoe design. Like the cap-toe, it’s sleek and dependable; unlike the cap-toe, its vibe skews a tad more insider-y—if you’re wearing a pair, you’ve probably got a handful of other dress shoe options at home. For close to 150 years, Church’s, the Prada-owned Northampton institution, has been churning out footwear that’s luxurious without rubbing your face in it. Its Chetwynd wingtips, made in the UK from premium mocha brown leather, represent the brand at its best: old-world craftsmanship combined with an eye towards the hustle and bustle of the urban sprawl.
What if we told you some of the best wingtips on the market happen to be available via an online behemoth more famous for its express shipping than its selection of formal footwear? (We know, we could scarcely believe it either.) When you hear us waxing on about bang for your buck, this is exactly what we mean.
The Best Monk Strap Dress Shoes
If the wingtip is a Lexus, the monk strap is a screaming red Porsche. Monk straps have been around in one form or another since the late 15th century (perhaps you remember their early-2010s heyday?) and there’s still few dress shoes that’ll imbue your work fits with the energy of a wheeling, dealing power player as effectively. Crafted in the UK with silver buckles and set on a Goodyear-welted rubber sole, John Lobb’s double monks are the ideal complement to a chalky peak lapel suit or a pair of cream-colored slacks and a pale blue dress shirt. Rolling to work in these bad boys is like pulling up to the PTA meeting in a flashy drop-top. They might not be for the faint of heart—or wallet—but if you can fork over the coin they’ll make you feel like a capital-B boss every time you strap ’em on.
Though they might conjure up images of well-heeled Italian gentleman sucking down Marlboros outside of Pitti, today monk straps are a truly global affair. Case in point: These beauties from Suitsupply, the Dutch suiting stalwart that also knows its way around some stellar footwear, and these toasted joints from Ralph Lauren, the archetypal American brand that needs no introduction.
The Best Dress Boots
When occasion calls for the formality of a dress shoe but Mother Nature has other plans, a dress boot—the dress shoe’s swole older brother—is the only way to go. Don’t be the dude stomping around the subway platform in galoshes, or worse yet, hastily-tied plastic bags. Prove to the world you’re better than that by scooping a pair of Grenson’s Hadley boots, a classic derby silhouette plopped on top of a lightweight commando sole engineered to tackle whatever the weather has in store. Made from handsome natural grain leather that’ll play nice with winter-weight dress pants and heavily-cuffed chinos alike, they beat stuffing your dress pants into a pair of enormous rubber Wellies 100% of the time, every time.
Interested in a pair of dress boots that offer all the appeal of your go-to wingtips, only taller? Give Thursday Boot Co. a try. Need a shoe that’s heavy on function without compromising on form? Eastland’s Ethan boots come with hefty Vibram soles that’ll help your pant hems stay muck-free on your trek home from the subway.
The Best Dress Shoes for a Night Out
Toga Virilis’ tricked-out brogues are what happens when a dress shoe grows up, goes to college, reads a little Goethe, and comes back from its semester abroad with an affected accent and a vinyl copy of London Calling. The kiltie detailing alone would be enough to turn heads, but the silver-tone hardware really clinches it: your dad’s old work shoes these ain’t. You might not wear them to a board meeting, but if you’re angling to add a little hard-won street cred to your dress shoe repertoire—and snag some footwear that’ll automatically up the ante on whatever else you’ve got on—you couldn’t do much better than starting with these.
Dress shoes you can confidently hit the town in should still feel luxe, but they should also be able to take a beating. Look for not-so-subtle flourishes—artful flecks of paint, pristine white uppers, for example—to help take your footwear firmly into Big Flex territory.