Most Comfortable Men’s Dress Shoes 2023

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


Sizes: 5-16 | Widths: AAAA-EEE | Colors: Dark Chili, Black, Walnut Brown, Coffee Brown, Mahogany, Burgundy Leather | Upper Material: Calfskin | Sole Material: Leather

This classic shoe—first introduced in 1982—is frequently touted by both stylists and podiatrists due to its sleek silhouette and supportive fit. While so many comfortable dress shoes skew vaguely orthopedic, this iconic lace-up oxford is cushy and forgiving yet visually minimalist: It features an updated low profile, leather-lined interior, cork insoles that mold to your foot and it’s available in ten different widths.

Most Affordable Comfortable Men’s Dress Shoes

Cushioned Style For A Modest Price

Sizes: 8-14 | Widths: M | Colors: Tan, Black | Upper Material: Nappa full grain leather | Sole material: Leather and rubber

This more casual dress shoe has a memory foam-cushioned footbed to make it springy, and the rubber sole offers traction while commuting across cement-lined streets, subway platforms, or on slick office flooring. While this shoe only comes in a medium width, it’s a little more forgiving than other, stiffer shoes and it runs slightly wider in the forefoot for added comfort, according to Howard Friedman, MD, podiatrist at Suffern Podiatry.

Most Comfortable Men’s Dress Boots

Ankle Boots With Comfortable Soles

Sizes: 6-14 | Widths: M | Colors: Dark Brown Scotch Grain, Black Scotch Grain | Upper Material: Calf leather | Sole Material: Rubber

British shoe manufacturer Crockett and Jones has been making men’s footwear since 1879, with designs ranging from sporty chukka boots to elegant velvet slippers to versatile derbys. This pull-on pair’s almond-shaped toe allows feet room to spread out, and its water-resistant welt and cleated Vibram rubber sole make it springy, durable and the perfect traction for slick winter sidewalks.

Most Comfortable Men’s Business Casual Shoes

Understated, Casual Cool

Sizes: 7-13 | Widths: M | Colors: Brown | Upper Material: Calf Leather| Sole Material: Rubber

Luxury Italian shoemaker Santoni is possibly best known for their handmade high-end oxfords and derbys, which are boardroom favorites. This casual take on a classic—it’s an elegant sneaker-derby hybrid—can be worn with everything from dress pants to khakis to jeans. While these shoes have a slightly tapered shape, some say they run large so take that into consideration when picking your size.

Most Comfortable Men’s Dress Shoes For Standing All Day

Elevated Shoe With Cushion And Flexibility

Sizes: 7-14 | Widths: M | Colors: Black, Marine Blue | Upper Material: Fabric and leather | Sole Material: Rubber

Cole Haan is at the top of foot specialists’ lists for comfort, and this pair has hundreds of positive reviews. While the fabric construction is slightly informal, the tight weave is more sophisticated than a sneaker and the responsive material allows feet and toes room to spread out. The special soles have pumped up cushioning, foot-friendly flexibility and they’re lightweight. Another bonus: These offer a great fit and comfort right out of the box.

Most Comfortable Men’s Slip-On Dress Shoes

Extreme Comfort From A Luxury Brand

Sizes: 5-15 | Widths: M | Colors: 17 colors, from muted neutrals to bold brights (available at a variety of retailers) | Upper Material: Suede | Sole Material: Rubber

These unassuming, hand-stitched slip-ons are so popular it can be difficult to get your hands on a pair. Their low-profile white sole is springy and forgiving on feet and joints, and the supple full-grain leather is flexible if you’ll be doing lots of walking. We especially love that the sneaker-meets-dress-shoe construction makes them appropriate for a variety of outfit choices—paired with khakis, slightly rolled jeans or stylish suiting.

Most Comfortable Men’s Black Dress Shoes

A Versatile Classic

Sizes: 7-13 | Widths: M | Colors: Cuoio, Black | Upper Material: Leather | Sole Material: Leather

If you’re the guy who still wears a suit to work, this subtle, understated, goes-with-everything shoe is your go-to. Despite a refined silhouette, this pair allows for a little more room near the bridge of your foot and at the toe, so the fit doesn’t feel constricting. Wearers like that the leather is supple and molds to the foot, so this pick is comfortable whether you’re meeting with clients, standing at a cocktail party or running to catch a train.

Most Comfortable Men’s Dress Shoes For Wide Feet

Elegance Paired With Durability

Sizes: 7-14 | Widths: D, EE | Colors: Black, Oxblood, Walnut | Upper Material: Leather | Sole Material: Leather, rubber

Not brands make wide widths but Anthony Veer offers accommodating shoes that are both good looking and reasonably priced. This stylishly perforated brogue is leather-lined with a lightly cushioned insole; plus, its “Goodyear welt construction”—the gold standard of shoe construction—means the sole is durable and can be easily replaced when you eventually wear them down. Just note: Some reviewers say these run large.

Most Comfortable Men’s Dress Shoes For Walking All Day

Lace-Ups For On-The-Go

Sizes: 7-15 | Widths: M, W | Colors: Black Pebble Grain, Brown Pebble Grain | Upper Material: Leather | Sole Material: Vibram rubber

The Samuel Hubbard shoe company was founded in 2013 by Bruce Katz, whose family launched Rockport in 1971. Katz clearly knows the secret to creating comfortable shoes: If you’re going to be on your feet for hours, you need to start with a good, flexible foundation. These derbys have a Vibram sole that’s both lightweight and durable, and a breathable memory foam insole that’s removable if you prefer a custom insole or orthotics. You’ll be painless and polished throughout the day, whether wearing these with a suit or jeans.

Most Comfortable Men’s Dress Sneakers

Casual-But-Transformational Dress Shoe

Sizes: 8-15 | Widths: M | Colors: Black, Grey, Hazelwood, Navy | Upper Material: Fabric | Sole Material: Rubber

Raleigh, North Carolina-based Peter Millar is a well-respected presence in the casual men’s sportswear space, and these shoes perfectly embody the brand’s sporty-elegant vibe. Thier textile mesh upper is supportive and breathable, they have a padded tongue and removable foam insole with extra cushioning as well as a shock-absorbent midsole. The elastic laces are customizable, and the rounded toe allows movement and breathing room. Style tip: The black and navy tend to read dressier than the lighter shades.

My Expertise

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.

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