The most comfortable men’s dress shoes are the formal(ish) ones you wear to work, weddings and parties when sneakers won’t fly. As is the case with many types of shoes, there are good and bad ones out there. The wrong dress shoes are stiff, painful to wear and look like they belong in a time capsule from the 1950s. The best dress shoes, on the other hand, mold to your feet, feel great and fit in with other stylish items in your closet. To find out what separates the torturous from the truly excellent, we consulted experts who spend a lot of time on their feet and prioritize comfort (and good looks) in footwear.
Ahead, you’ll find all the pairs we highly recommend. Our picks for the Most Comfortable Men’s Dress Shoes Overall (the Allen Edmonds Park Avenue Cap Toe Oxford) and Most Affordable Comfortable Men’s Dress Shoes (the Johnston & Murphy Lewis Plain Toe) not only have outfit-making potential, but they’re also nearly as comfortable as your everyday sneakers. You can read more about how we made these selections at the end of this guide, and for more on men’s fashion, check out our stories on best men’s dress shirts and best men’s jeans.
Most Comfortable Men’s Dress Shoes Overall
Supreme, Sartorial Comfort
Most Affordable Comfortable Men’s Dress Shoes
Cushioned Style For A Modest Price
Most Comfortable Men’s Dress Boots
Ankle Boots With Comfortable Soles
Most Comfortable Men’s Business Casual Shoes
Understated, Casual Cool
Most Comfortable Men’s Dress Shoes For Standing All Day
Elevated Shoe With Cushion And Flexibility
Most Comfortable Men’s Slip-On Dress Shoes
Extreme Comfort From A Luxury Brand
Most Comfortable Men’s Black Dress Shoes
A Versatile Classic
Most Comfortable Men’s Dress Shoes For Wide Feet
Elegance Paired With Durability
Most Comfortable Men’s Dress Shoes For Walking All Day
Lace-Ups For On-The-Go
Most Comfortable Men’s Dress Sneakers
Casual-But-Transformational Dress Shoe
For this story, I spoke with three foot and footwear specialists: Colin Dombroski, PhD, author of The Plantar Fasciitis Plan: Free Your Feet From Morning Pain and founder and clinical director at orthotic and footwear company SoleScience; New York-based men’s fashion stylist Turner Allen, founder and lead stylist at Style Turner; and Howard Friedman, DPM, podiatrist and owner of Suffern Podiatry. They discussed things to consider when shopping for comfortable dress shoes, how to find the best fit, and the specific pairs that combine comfort and style. Their unifying message: Finding a great dress shoe isn’t just about picking something you like in your size, it’s about finding a fit that accommodates the entire shape of your foot.
How I Chose The Best Men’s Comfortable Dress Shoes
To determine the best comfortable dress shoes for men, I first informally surveyed the men I know to learn about their favorite comfortable shoe styles, brands and models. I considered shoes highly recommended by podiatrists, and I evaluated the models highlighted by the experts I spoke with. Finally, I read hundreds of customer reviews of men’s dress shoes at a wide variety of price points. I ultimately chose the best comfortable dress shoes by evaluating whether they successfully met most of the following criteria: universality of fit, size availability, width availability, adjustability, degree of cushioning from a liner or sole, flexibility and overall versatility.
What To Consider About Dress Shoes
As with many things, men’s dress shoes have become more casual overall post-pandemic. “Since most men no longer have to wear a suit and tie every day, oxfords are less popular, and derbys and loafers are in,” says Turner. “Simple designs are the most appealing because they’re the most versatile.”
“It’s important to remember that you have a foot shape, not just a shoe size,” says Dombroski. “You have to focus on fit most of all. You may measure a certain size, but that size is only a starting point of your length, width and depth.” Also, if you haven’t been measured in a few years, it’s a good idea to go into a shoe store to get professionally measured: “It’s typical for a person’s foot to elongate and widen over time,” says Friedman.
To ensure you have the best fit, the experts we spoke with recommend taking the following steps when trying on dress shoes:
- If possible, remove a shoe’s liner and stand on it, says Friedman. This way you can visually see if it accommodates both the length and width of your foot to ensure you won’t experience rubbing on the sides, front or heels.
- Try on shoes with the socks you plan on wearing with them, says Friedman.
- If a dress shoe is uncomfortable at the outset, move on. “If it’s squeezing your toes, that’s not going to improve with time,” says Friedman. “It likely won’t ‘break in,’ and your foot is going to suffer. It will get blistered and, with repetitive use, the area will callous and you may experience prolonged discomfort.” You’ve been warned.
Shoe Shape and Width
Not all shoes come in wider widths, so if you have a wide foot or prefer a little more room at the bridge of your foot, try to find a style that can accommodate you. In general, a rounded toe will be more comfortable as opposed to pointed styles. “Your toes splay while you’re standing and they need room to move,” says Friedman. “They can function better and will be more comfortable if they’re not encumbered.”
Sole and Insole
Soles are made of leather or rubber, and while leather has some give to it, rubber soles offer more flexibility and springiness. “Vibram rubber soles are more durable and comfortable [than leather], especially for men living in cities where driving isn’t the norm,” says Allen. “Lug soles are a client favorite because they can easily withstand different terrains.” Dombroski agrees: “Most people bear their weight on the heels and balls of their feet,” he says. “Rubber soles absorb shock better. They grab more traction and offer more comfort on a high stress area, specifically the balls of your feet.”
Another factor that can significantly affect comfort is an insole liner. “A liner acts as a buffer,” says Friedman. “Some liners have cushioning and arch support built into them. Look to see if there’s a removable liner, especially if you use orthotics.”
Slip-On Versus Lace-Up
Dress shoes with laces tend to be the most versatile. “The advantage of laces is that they allow you to make adjustments to the shoe,” says Friedman. “ You can make it looser in the front or keep snug on the top so it reduces slippage.”
If you work in a creative or more casual field, slip-ons are a stylish and comfortable choice since they often come with rubber soles. However, “if you have a high instep and voluminous foot, you may find slip-on shoes uncomfortable because you can’t adjust that part of the shoe,” says Dombroski.