12 Most Comfortable Dress Shoes For Men In 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 match the 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.

The most comfortable dress shoes for men are sleeker and more stylish than you'd think

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. Read more about how we made these selections at the end of this guide, and for more men’s fashion advice, check out our guides to the best men’s dress shirts and best men’s jeans.

Allen Edmonds

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.

Macy's

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.

Amberjack

Sizes: 7-15| Widths: M | Colors: Black, Color Eight | Upper Material: Leather | Sole Material: Rubber

Designed in Brooklyn and made in Portugal, Amberjack’s dress shoes are popular among guys for their affordable, high-quality leather construction and sneaker-like details. This full-grain leather pair arrives already feeling broken-in and has an athletic outsole and sheepskin lining that’s perforated to encourage air flow (you can even wear these shoes without socks if you prefer).

Beckett Simonon

Sizes: 7-14 | Widths: M | Colors: 5 total, including Black and Tan | Upper Material: Leather | Sole Material: Leather, rubber

Beckett Simonon’s Oxfords are made to order with thoughtful details that add serious comfort: The almond-shaped toe box gives your toes room to spread out, the tapered footbed provides arch support and the leather insole molds to your foot for a custom fit. The entire shoe is crafted from full-grain leather that’s durable yet soft and smooth, right out of the box. Also great: The leather lining absorbs sweat and controls odors.

J.Cew

Sizes: 7-13 | Widths: M | Colors: Black, Color Eight | Upper Material: Leather | Sole Material: Rubber

J.Crew has an extensive range of formal-ish men’s footwear, with designs ranging from sporty chukka boots to versatile loafers. This pull-on pair’s almond-shaped toe allows feet room to spread out, and its water-resistant welt and Vibram rubber sole make it springy, durable and the right traction for slick sidewalks.

Saks Fifth Avenue

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.

Nordstrom Rack

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.

Loro Piana

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.

To Boot

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.

Macys

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.

Nordstrom

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.

Peter Millar

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.

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.

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.

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.”

Fit: “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:

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.

The answer depends on your needs and what type of office environment you work in. For most men, Allen Edmond’s dress shoes are a top choice among stylists and podiatrists thanks to their sleek silhouette and supportive fit. Essentially, the brand’s shoes have a streamlined look that works in any dress code and comfortable designs that can be worn all day. For a more casual option, Peter Millar’s sneakers strike the right balance between formal and laidback with athletic features. Cole Haan is another excellent choice and an example of a footwear brand focused equally on comfortable construction and stylish aesthetics.

Several popular brands have men’s dress shoes in varying widths, including Johnston & Murphy, Allen Edmonds, Rockport, Stacy Adams and Cole Haan. Another way to make a shoe wider, experts say, is to remove a shoe’s insole to allow your foot to have room to spread out. “If a shoe doesn’t come in a wide width and you need slightly more space, removing the insole can potentially gain extra space if you need it,” says Dombroski.

There are a few simple guidelines, says Dombroski:

1. “First, you should have a bit of room—about a quarter of an inch—between the end of your longest toe and the end of the shoe to accommodate for movement and swelling throughout the day,” he says. “If it’s a running shoe you may want a bit more space, but not necessarily with a dress shoe when you’re sitting for a good portion of the day.”

2. “The shoe width shouldn’t feel constricting,” he says. “You should be able to wiggle your toes slightly.”

3. “Take out the insole of the shoe, and then stand on it on the ground,” says Dombroski. “Does your foot fit within the outline of the insole? That’s a pretty good indication. If your fourth and fifth toe aren’t fitting, move on.”

Absolutely. “Rounded, English-style toes, pebbled leather, and chunky soles are casual and easy to wear in both dress and informal environments,” says Allen. Dress shoes like derbys, brogues, slip-ons or loafers can be worn with anything from denim to khakis to a variety of dress pants and suiting.