Before 2020, I suffered in dress shoes, bled in them, developed blisters and bunions, always willingly. Comfortable, practical, and easy were words I simply ignored. I liked my monk straps and derbies tight and constricting, and wingtip oxfords with heavy platforms. The shoes I chose over the rest, though, were ankle boots, usually with pointed toes and heels that were at least two inches. Sounds painful, right? Well, they often were. I wore anything that polished my look, gave me height, and added character. I didn’t care about discomfort.
But things have changed. The last time I wore proper dress shoes was last summer at a friend’s wedding. I clearly had racks and racks of them, but the week before, I decided to purchase a pair of printed penny loafers with a wide shank and added cushioning, because feeling comfortable was the priority. I couldn’t wear sneakers, let alone the Uggs that I grew accustomed to, so I found a shoe that was the next best thing. It felt like I was walking on clouds the entire time.
Indeed, what constitutes no-fuss, painless footwear changes with every person. But if you’re looking for categorically comfortable dress shoes, look for styles that were engineered with extra support, have silhouettes that provide greater ease and mobility, and feature shock-absorbing midsoles and outsoles that help with balance. I’m not talking full-on orthopedic shoes here; something snazzy that makes a statement should always be on the table (or, er, on your feet). I am, however, talking about shoes that won’t let you suffer in the least, that were built to allow you stand for hours on end, all while adding character to your fit.
Should you have a wedding, cocktail party, or other fancy shindig on the horizon, and want comfortable dress shoes to wear, check out 10 of the best below. Your feet will thank you immeasurably.
Whiddon Pace Oxford Shoe
We know and love Clarks for its storied dessert boots—some of the comfortable shoes around. Its “oxfords”—though, they are really derbies, thanks to the open-throat construction—fit the same bill. This sporty option, for example, doesn’t only feature a bicycle-toe design, but is built with a removable Ortholite footbed that wicks away moisture and absorbs impact.
Harrison Monk Strap Shoe
When it comes to comfortable shoes, Vionic is the name to know. The brand’s collections are made with the input of podiatrists, and feature rubber outsoles for great traction and removable footbeds that help provide cushioning and arch support. And this monk strap shoe with kiltie detailing is no exception.
Medfield Cap-Toe Oxford Shoe
If the exterior of this Florsheim “oxford” (again, it’s really a derby), with its genuine leather upper in rich cognac doesn’t get you, the interior, with a fully cushioned insole and shock-absorbing foam, should.
Original Grand Wingtip Derby Shoe
This wingtip derby features Cole Haan’s signatue Grand.OS technology, which provides anatomically engineered cushioning, along with a grooved rubber sole for greater traction.
ST1 Hybrid Plain-Toe Derby Shoe
The Phorene midsole with responsive Fluidform technology in Ecco’s footwear—including this dégradé derby—is not only light and soft, but also shock-absorbing.
‘Federico’ Oxford Shoe
For over seven decades, Spanish brand Magnanni has crafted the finest dress shoes, finished off with hand-made details. And the looks are only matched by the comfort, provided by the extra cushioning in the insole.
Tipping Point Shoe
Samuel Hubbard offers up wingtip derbies with custom Vibram soles for support and balance, and triple-density memory foam footbeds for the utmost comfort. Expect your feet to feel coddled with these shoes on.
‘Marlon’ Derby Shoe
When Mephisto was founded in 1965, comfort was at the core of the company. The French label consistently offers dress shoes, like this pebble-grain derby, that are built for standing and walking long hours. This is because of its unconstricting silhouettes, which are great for men with wide feet, and durable Goodyear-welt construction.
Penny Loafers
Tod’s is known for its driving shoes, called Gomminos, with pebbled soles that give those behind the wheel greater ease when pushing the pedal to the metal. This sleek penny loafer takes the same base, but enlarges the pebbles and adds a thick heel for great balance and comfort while walking.
Horsebit Loafer with Web
The Gucci Horsebit loafer is one of the most iconic shoes in history, worn by the most stylish gents around and updated regularly. A recent refresh has placed a greater value on comfort, evidenced by the fold-down heel. After all, what’s more comfortable than a slipper?
Barry Samaha
Barry Samaha is the style commerce editor at Esquire, where he covers all things fashion and grooming.
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