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By Avidan Grossman , Gerald Ortiz , and Michella Ore
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In 2024, figuring out where the best dress shoes for men fit into your footwear rotation can be a little confusing. 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 2024? 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 months 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.
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 sport coat and faded jeans as it will a hefty cable-knit and slouchy dress pants.
"Valencia" Wholecut Shoes
If the Aldens are a little outside your price-range, Beckett Simonon’s wholecut dress shoes are a great option at a quarter of the price. They're crafted from a single piece of leather, a process that normally costs several times what they’re charging, and built with a resolable blake stitch construction.
George Cleverley Leather Oxford 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 flourishes 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.
"Melton" Cap Toe Shoes
No, a leather lace-up will never be as comfortable as a running shoe. But if cushioning is a primary concern, Johnston & Murphy's classic cap toe is a mighty handsome and comfy option for below two Benjamins. The cushy interior will treat your dogs like the pampered pooches they are thanks to the type of arch support that makes podiatrists swoon. Same goes for Banana Republic’s excellent cap-toes, which are crafted from a smooth leather in Portugal and held together by hardy waxed laces that definitely won’t unravel on you when you make it to your interview with minutes to spare.
Strand Cap Toe Oxford shoe
The brogue takes its name from the distinctive perforations (or "broguing") found on the toe and outer edges of the style. And like so many of its pedigreed footwear peers, Allen Edmonds makes an absolutely killer pair. The iconic American brand specializes in refined dress shoes and boots that are built with high-quality leathers and Goodyear welted construction. The Stand is one of the brand's most popular shoes with its classic captoe styling and brogue details and it comes in several colorways to complement any wardrobe palette. This deep chili colorway is great for navy, grey, and brown suits, but if you want to take it out of the formal context, they'll also look pretty great with a vintage pair of jeans.
Ellsworth Medallion Plain Toe Wholecut Shoe
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. Thom Browne's longwing version has become a house signature for a reason, but if you're looking for an option with a dinner party-worthy backstory, Not to be outdone, Johnston & Murphy's higher-end sublabel produces the Ellsworth shoe, a wholecut dress shoe with elegant brogue detailing and Goodyear-welted construction, all for just below three bills.
"Burwood" Wingtip 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 Burwood wingtips, made in the UK from premium inky-black 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. Naturally, the French cobbling legend at J.M. Weston also sell a killer version, kitted out with Guilloche piping and a triple-layer outsole that makes you feel like a not-so-short king and will see you into your retirement.
"William" Monk-Strap Leather 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.
If you’re looking for shoes with a touch more niche appeal, head straight to Morjas. Founder Henrik Berg weaves together Mediterranean and Scandinavian influences that yield a pair of chocolatey suede beauties with double monk details. On a slightly more rugged and, dare we say, punk end of the derby spectrum is Solovair. They're the original factory that manufactured Dr. Martens shoes back in the day and they're still cobbling up a storm, producing classic dress shoes as well as more rugged options like the single buckle monk shoe. The shoes are produced in England with a comfy and resolable rubber sole and a glossy leather upper.
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 R.M.Williams Comfort Craftsman boots, a classic Chelsea boot silhouette plopped on top of a lightweight dainite 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. It's hard to believe that a shoe with such chiseled and refined features was originally built to tackle the rigors of the Australian outback, especially when it looks quite at home with a slick suit.
If R.M.Williams is a bit out of your budget, Astorflex is another great option at about half the price. All of Astorflex's shoes are made in a generations-old shoe factory in Italy with vegetable-tanned leathers and blake stitch construction. The Bitflex Chelsea is a slightly more rounded take compared to the Craftsman, but give it a quick buff and shine and you're ready to take them with you to the board room. For something with an equal amount of ruggedness and refinement, the Kingsman x George Cleverley Cap-Toe Pebble-Grain Leather Boots offer a countryside appeal with plenty of tableside manners.
Unlike most dress boots, chukkas don't really have a low-top counterpart. Chukkas are similar to desert boots in their upper construction but are noticeably dressier since they're made with leather soles rather than rubber crepe ones. Chukka boots were originally made for horse-riding military men and eventually became part of the discerning gentleman's civilian outfit. Thursday Boot Company's Scout Chukka is a great entry-point option that uses nice leathers and solid construction, a bargain considering its $160 price tag.
Murphy Goodyear Welted Chukka Boot
But if you've got some more spending power, Drake's Murphy boot is a great choice. It's constructed like a high-quality dress shoe but its luxe-leaning coffee suede lends it a versatility other chukkas can only hope to approximate. Oh, and if money's of no concern? Take Edward Green's Banbury boot for a spin. The master shoemaker is largely considered a final boss of the footwear space, and his sleek, cantilevered stompers do nothing to dissuade us of his reputation.
In 2024, your loafers should toe the line (ha!) between sneakers and dress shoes, traversing black tie events and bodega runs with equal panache. The king of the genre is Gucci's horsebit model, introduced in 1953 and still painstakingly crafted in the brand's factory just outside of Florence. In the years since its debut, the bit-laden slip-on has galloped its way into the annals of menswear history as the loafer of choice for style-minded fellas looking for a luxe option with nearly as much cachet as a Rolex (it's no coincidence that both make for perennially swanky graduation gifts). They'll look exquisite with a slouchy charcoal suit, sure, but they're just as dashing with vintage jeans and a rumpled button-up.
G.H.Bass & Co
If all that equestrian-inspired hardware feels a tad much, a classic pair of penny loafers, the kind you see splashed over the pages of Take Ivy, will never steer you wrong. They're equally as versatile as their fustier counterparts—and you won't have to worry about matching your jewelry to your kicks. G.H.Bass & Co. was the brand that introduced the style to the States and has since cemented its version as the quintessential penny loafer. Alternatively, you can slip on a pair of Bode’s buttery-soft house slippers and feel like the posh little prince you are—then transition to Tom Ford’s sleek and sexy Martin loafers when it’s time to commune with the masses.
The best men's dress shoe brands tend to be the ones that have been around the longest. Brands like Allen Edmonds, Alden, Crockett and Jones, and J.M.Weston have been making shoes for generations and continue to do so to a very high degree. They're made in factories by skilled craftspeople using top-quality leathers and old-school, time-tested methods which often require several hundreds of steps each process. That craftsmanship is typically reflected in the price, which can start $400 and go all the way up to a cool grand.
That being said, other brands that have generations of shoemaking under their feet have expanded their operations to produce shoes faster and more cheaply. (Brands like Cole Haan, Florsheim, and Johnston & Murphy are some of the most popular among them.) And while many of them modern brands make sneaker-dress-shoe hybrids, they also offer some stylish classics at affordable prices—a great in-between option for anyone on a budget. Plus, many of these brands also still make shoes with a high degree of craftsmanship (and a higher price tag), often distinguished as a fancier sub-label that calls back to its heritage.
These days, though, there are many young brands putting their foot in the dress shoe game, too. While a lot of them are more or less duds, the ones we like are using great materials and building their shoes in factories with a long history of shoemaking.
There are several ways to answer this. The first and cheapest option is to get a pair of dress shoes that are built like sneakers. These types of dress shoes are also built more cheaply, so while they might not last as long, they are lighter and come with rubber soles and/or foam insoles, so they will feel more comfortable straight out of the box.
On the total opposite end is to get a pair of fully bespoke shoes. A master shoemaker will make a custom last built to your exact foot shape rather than an off-the-rack pair of dress shoes which are a one-size-fits-most situation.
In between those two options, good-quality leather dress shoes will use some kind of cushioning in the sole, often with a high-quality leather insole and a cork filling, both of which will mold to your foot. They will also use a shank inside the shoe to provide stability and arch support.
The best way to ensure you have the right size dress shoe is to go to the store and try them on in person. If possible, try at least three different sizes: the size you think you are, and a half size larger and smaller. Remember to ask the sales associate if the shoes you're considering come in different widths.
Make sure your toes aren't pinching and that they have enough room to spread. The balls of your feet shouldn't feel cramped; that will be the point where the shoe flexes with each step. Be aware of heel slippage as well—it's common to have a bit, but if you can fit a finger in the back of the heel comfortably, your shoes are probably too big. When trying on a pair of dress shoes, remember to wear the same socks you would normally wear with them so you can accurately account for sock thickness, too.
Durability comes down to material and construction. High-quality, long-lasting dress shoes will use full-grain or top-grain leather uppers. They will be constructed in such a way that allows the shoes to be easily re-soled by a cobbler, either with blake stitching where the uppers are sewn directly to the outsole, or with a Goodyear welt where the uppers are sewn to a leather welt that wraps around the shoe…which is then attached to a leather or rubber outsole. Many cheaper dress shoes use thin leathers and are constructed by simply gluing the upper to the sole, like on sneakers. This gluing method is cheaper and oftentimes more comfortable, but is very difficult for a cobbler to resole.
The Best Boots for Men, From A to Z
The Best Loafers for Men to Crush All Your Summer Fits
The Best Chelsea Boots for Men to Wear With Everything
The Best Sandals for Men Will Make Your Summer Even Hotter
The Best Dress Shoes for Men Are More Essential Than Ever
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