35 Best Dress Shoes for Men in 2022: Plain-Toe, Cap-Toe, Brogues, Monk Strap, and More


It will be more difficult than ever to find the right dress shoes for men in 2022. Adidas is the brand your friends love. Your coworkers are hesitant to take off their Allbirds. Everybody is wearing Crocs. (Crocs!) It’s not easy to find room in your heart or closet for shoes that you once associated with the grind of your 9-5.

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But here’s a problem: today’s most compelling dress footwear doesn’t feel the exact same as the ones they replaced. The craftsmanship is there, sure, but how about the fussiness? It’s not so much. It’s almost rebellious to choose a dress shoe over endless other options. Dress shoes will always be a staple in your work wardrobe and a favorite for formal occasions. However, they can be surprisingly versatile in their Platonic form. hip. Sexy, even.

This brings us to the next point of business: IsWhat about a dress shoe in 2022 The Derbies are the perfect choice. But do Chelsea boots? What about loafers? The answer is simple: yes. All of those options will work if the destination isn’t a good fit for convention. Sometimes, however, circumstances call for a more traditional silhouette. You’ll be glad that you turned here.

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. They will not let you down, whether you are wearing them to your very first in-person meeting in almost two years or to your very first date in nearly three years. Going WithThe (pebble) grain has never looked so good.

The Best Plain-Toed Dress Shoes

Alden plain-toe blucher 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. The investment will pay off in the long-term if you are willing to spend the money now. Each pair of shoes could be the last of its kind that you ever buy. (Assuming of course that you have the necessary 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 brand’s most iconic style, the blucher, looks equally good with a tweedy jacket and faded jeans as with a thick cable-knit and slouchy pants.

Magnanni “Melich II”Shoes with a plain toe

Beckett Simonon “Valencia”Wholecut shoes

If the Aldens are a little outside your price-range, Magnanni’s handmade plain-toe derbies are a stellar substitute—for roughly half the price. 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

George Cleverly leather Oxford shoes

Do you need a pair of dress shoes that you can wear to a wedding or funeral, job interview, court appearance, or other events? (No judgment here, pal!) A black cap toe is a sure bet. You can trust the jack-of all-trades style and feel confident that you won’t be breaking any socially-imposed dress code wherever you go. There are many choices, but George Cleverly’s are the best. They’re made in England by hand and are meticulously detailed with every detail. Get married in ’em if you choose—heck, get buried in ’em, too. But you should get a pair.

Allen Edmonds Fifth Avenue cap toe oxford heels

Johnston & Murphy “Melton” cap toe shoes

A leather lace up will never be as comfortable and supportive as a running shoe. Allen Edmonds’ signature inserts will provide cushioning if that is your primary concern. Are you hesitant about spending the big bucks on a formal shoe? Johnston & Murphy offers a classic cap-toe for less than two Benjamins.

The Best Brogue Dress Shoes

Tricksters “Bourton”Brogues by derby

The distinctive perforations of the brogue (or) are what give it its name. “broguing”The style has a branded logo () on the toes and outside edges. Trickers, like many of its pedigreed footwear peers makes a truly outstanding pair. The British brand specialises in elegant, well-made dress shoes that aren’t too precious. Many of its shoes are built on top of durable Dainite soles that you can wear for years. The Bourton derby, in a rich, black-y shade, is specially designed to transform your navy suit into street style inspiration in 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.

Thom Browne wore longwing brogues with pebbles


Thistle Shoes “Ghillie” brogues

Nearly every cordwainer worth naming makes solid brogues, so it’s easy to find one that won’t break the bank. Thom Browne has made the longwing version a household favorite. But, if your looking for a brogue with a story to impress guests at dinner, Thistle Shoes offers brogues inspired from traditional Scottish footwear. These brogues are reinforced with steel quartertips and all-terrain soles and are the dress shoe equivalent for four-wheel-drive.

The Best Wingtip Dress Shoes

Church’s “Chetwynd”Leather wingtips in lace-up

The wingtip is named after the wing-shaped broguing which runs from the silhouette’s heel to its toe cap. 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. Church’s Northampton institution owned by Prada has been producing footwear that is luxurious and doesn’t rub your face. The brand’s Chetwynd wingtips are made in the UK out of premium chocolate-ybrown leather.

Loake “Chester”Calf leather wingtips in burnished color

Florsheim “Lexington”Oxford wingtips

What if we said that some of the most sought-after wingtips are available through an online retailer more known for its fast shipping than its selection formal footwear? (We can’t believe it. We mean exactly what we say when we talk about bang for the buck.

The Best Monk Strap Dress Shoes

John Lobb “William”Double monk strap leather shoes

The monk strap is a screaming Porsche if the Lexus’ wingtip is the Lexus. Monk straps have been around since the end of the 15th century in some form or another (perhaps you recall their glory days in the early-2010s). There are few dress shoes that will give your work outfits the same energy as a wheeling, dealing power player. John Lobb’s Double Monks are made in the UK and feature silver buckles. They have a Goodyear-welted rubber bottom and are the perfect complement for a cream-colored slacks or a pale-colored dress shirt. These bad boys are like a flashy drop-top bringing you to work. 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.

Suitsupply double Monk Strap Shoes


Ralph Lauren “Darnell”Monk strap shoes


Monk straps are now a global trend. They might conjure up images if you think of wealthy Italian men drinking Marlboros in the middle of Pitti. This is an example: These beauties are from Suitsupply, a Dutch suiting stalwart who also knows its way around some outstanding footwear. AndThese toasted joints are from Ralph Lauren, America’s archetypal brand.

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 that guy who walks around in galoshes on the subway platform, or worse, with plastic bags tied in hastily. Grenson’s Hadley boots are a classic derby silhouette that can be layered on top of a lightweight, waterproof sole designed to withstand any weather conditions. These boots are made from handsome natural grains leather that will go well with both winter-weight dress pant and heavy-cuffed chinos. They beat stuffing your dress pants into huge rubber Wellies 100% of every time.

Thursday Boot Co. wingtip Boots

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Eastland “Ethan” 1955 cap toe boots


Are you looking for dress boots that are taller than your wingtips? Thursday Boot Co. is worth a try. You want a shoe that is functional but not compromising on style? Eastland’s Ethan boot comes with thick Vibram soles to keep your pant hems clean on your return trip from the subway.

The Best Dress Shoes for Night Out

Toga Virilis polished Brogue Shoes

Toga Viilis’s tricked-out brogues show what happens when a dress shoes grows up, goes to college and reads a bit Goethe before returning from its semester abroad with an affect accent and a vinyl copy London Calling. The kiltie details alone would be enough to make heads turn, but the silver tone hardware really makes it stand out: these aren’t your dad’s old shoes. 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.

CamperLab paint print derby shoes


Dr. Martens 1461 “Bex”Shoes

Dress shoes that can be worn out on the streets should still feel elegant, but should also be comfortable. 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.

Plus 12 more Dress Shoes We Love

Stefan Cooke biker buckle-detail shoes

Never stress en errant shoelace again.

Adieu Type 54C derby shoe

A buffed-leather dress shoe can be made to feel more street-ready by adding a thick rubber sole. A thick rubber sole is the best way to make a buffed leather dress shoe more street-ready.

Crockett & Jones suede monkstrap shoes

Simple, clean monks that don’t make you look like an medevial friar

Edward Green “Cadogan”Brogues in burnished-leather

As tasty as the best cabs in any well-stocked wine cellar.

Meermin suede cap toe shoes

Made from leather imported from France, tanned in Italy and designed in Spain: Finally, dress shoes that are as stylish as you are.

Cole Haan split-toe Oxford shoes

Fair warning: Once you feel Cole Haan’s Grand soles, it will be difficult to force your feet into any other shoes.

TLB Mallorca calf-leat wholecut shoes

This is a rare opportunity to find premium vegetable-tanned calf skin leather at such a low price.

Manolo Blahnik “Witney” suede oxford brogues

Even the Oxford shoe can look downright beautiful when worn by a Spanish cobbler, whose heels are renowned for inspiring ardent levels if devotion.

Prada logo derby shoes

This sleek logo with the triangle is going to be the last thing you see on your way to securing a promotion.

Clarks “Un Tailor”Shoes with a plain toe

You’re right, the brand behind the most iconic desert boot on the planet also makes killer dress shoes.

Half hunt oxford shoes by JM Weston

What is that piece of material at the top of the vamp? This is called an “apron”. It is your ticket to a world filled with footwear-related compliments.

Carmina Chromexcel boots

Chromexcel boots by Carmina check boxes you didn’t know existed. Goodyear-welt construction? Perfectly rounded toe box Signature Soller last? Check, check, and again.

Cheaney “Avon C”Wingcap derby brogues

Hand-baked in the Northamptonshire factory of the brand.

Paul Stuart “Giordano”Monk strap shoes

If you choose to follow the single monk route, it’s best to stick with a company that has been producing them for gentlemen of impeccable tastes for well over eight decades.

Morjas plain toe blusher

Top of the line plain toes handmade in Spain with all the details you’d want in a dress shoe—sans the nasty sticker shock.

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