The most comfortable dress shoes for men are the formal(ish) ones you wear to work, weddings and parties when sneakers won’t fly. As is the case with many shoes, there are good and bad ones out there. The wrong dress shoes are stiff and painful. The right dress shoes, on the other hand, mold to your feet and feel great all day. After extensively testing the market and speaking to menswear experts, our top pick for the most comfortable dress shoes for men overall is Allen Edmonds Park Avenue Cap Toe Oxford. For a business-casual situation, Peter Millar’s Excursionist Penny Loafers are your best bet, and for a pair you walk miles in, we like Cole Haan ØriginalGrand Wingtip Oxfords.
The most comfortable dress shoes for men are sleeker and more stylish than you'd think. Man Casual Shoes
Our in-house male tester wore each of the shoes on this list for weeks, evaluating everything from fit to breathability to weight and wear. Ahead, you’ll find all our recommendations for the most comfortable dress shoes for men, along with expert advice on what separates the torturous from the truly excellent. And for more fashion advice, check out our guides to the best men’s dress shirts and best men’s jeans.
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.
What our tester says: “You can tell these things are made well. They are more of a traditional dress shoe and fit true to size, if you measure your foot correctly. This pair has a higher construction than other dress shoes and the leather does require some break-in time.”
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).
What our tester says: “These surprised me. I didn’t think I would be the biggest fan but I like the silhouette of the shoe and it’s very easy to dress it up and down. I struggled to keep my heel locked in the shoe without tying it really tight, but the heel is very comfy otherwise.”
Sizes: 6 to 15 | Colors: 9 total, including British Tan-Ivory and Blue Marine Nubuck | Main materials: Leather, textile | 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 sneaker-like sole is slightly informal, the wingtip Oxford design 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.
What our tester says: “These are so light and comfortable. They’re a good everyday dressier work shoe option, especially if you stand for long periods of time. I’m not sure how they will hold up over time, though—since they’re so light, the sole might wear quickly.”
Sizes: 7-14| Widths: M, W | Colors: 3 total, including Tan and Navy | Upper Material: Leather | Sole Material: Rubber
Florsheim is well-respected for their high-quality men’s shoes. The Frenzi Perf Oxford is made cushioned insole and a flexible outsole that provide a comfortable fit for all-day wear. The design is classic and stylish so you can dress this shoe up or down. Just keep in mind that nubuck leather requires regular care and maintenance to keep it looking its best. Some reviewers have noted that the shoe runs a bit large, so size down if you are unsure.
What our tester says: “I like the breathability of the Frenzi and the toe box is a little wider than some of the other options I tested. Just keep in mind that the style is a bit traditional—it reminds me of something my dad would wear.”
Sizes: 6-15| Widths: M, W | Colors: 7 total, including Maple and Black | Upper Material: Leather | Sole Material: Rubber
The Crossover is a good choice for guys who are looking for a shoe that can be worn for both work and casual occasions. It has an athletic sole, so you can walk long distances easily, along with a removable memory foam footbed for a plush feel. Also great: The interior has a chafe-free lining and the outer leather has been treated to improve softness, which cuts down on the break-in time. This pair also comes in wide and narrow sizes.
What our tester says: “These were the most comfortable of all the shoes I tested. The sole is firm with some give to it, but what surprised me most is how plush and breathable the inside is for it being a leather shoe. They’re well made and have a very clean aesthetic, and these will be a go-to option for me in spring and summer.”
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.
What our tester says: “These shoes fit perfectly and are my favorite shoe out of all the options I tested. They feel solid, comfortable without any gimmicks and provide good arch support thanks to the perfect fit. I think they have the best construction out of all the shoes I tried.”
Sizes: 7-15 | Widths: M | Colors: 8 total, including Black and Dark Chestnut| Upper Material: Leather | Sole Material: Rubber
Astorflex’s top-rated Chelsea boot is made with high-quality beeswax nubuck leather from Europe. It has an ergonomic footbed and 100% natural crepe rubber sole that’s soft and comfortable and each pair is handmade in Northern Italy by a family that's been making boots for six generations. Note that the boot comes in different types of leather, some of which like suede are not fully waterproof.
What our tester says: “I’ve been grabbing this dress boot over and over as a daily option. The crepe sole is extremely comfortable and the boot has almost no break-in period. My only dislike is that crepe sole can wear down faster than other options on this list.”
Peter Millar specializes in active casual shoes that can be worn on the golf course and beyond. This Excursionist has a classic penny loafer design with a clean and understated look. It’s made from supple water-resistant suede with a durable rubber outsole, so it can handle different surfaces. If you want a stylish and comfortable slip-on, this is the way to go.
What our tester says: “These penny loafers are a great warm weather or summer option. I like how easy it is to get them on and off without having to tie them. They run a little big so I’d recommend going down a half size if you want a sock-like fit.”
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.
What our tester says: “This is a nice simple option for a comfortable dress shoe. It's not the flashiest shoe but it’s straight forward and gets the job done. I would have liked a bit better leather quality but that would have raised the price for this shoe.”
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.
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.
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.
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.
Sizes: 7-14 | Widths: D, EE | Colors: Black, Oxblood, Walnut | Upper Material: Leather | Sole Material: Leather, rubber
Not all 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.
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.
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, writer Molly Calhoun 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, Calhoun first informally surveyed the men she knows to learn about their favorite comfortable shoe styles, brands and models. She considered shoes highly recommended by podiatrists, and evaluated the models highlighted by the experts she spoke with. Next, she read hundreds of customer reviews of men’s dress shoes at a wide variety of price points. She ultimately chose the best comfortable dress shoes by evaluating whether they successfully met most of the following criteria: universality of fit, size and width availability, adjustability, degree of cushioning from a liner or sole, flexibility and overall versatility. From there, the Forbes Vetted team tested the top picks firsthand, enlisting the feet and critical opinion of our group product manager, who wore the shoes for a period of a few weeks, taking notes on the pros and cons of each.
Our tester wore each pair of shoes, evaluating everything from comfort to weight to sizing.
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 fashion stylist Turner Allen. “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 foot expert Colin 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 podiatrist Howard 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.”
Our tester appreciated how Beckett Simonon's dress shoes come with a dust bag and removable insoles ... [+] to add extra comfort.
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.
Wolf & Shepherd's Crossover dress sneaker has an easy slip-on design, which our tester found ... [+] comfortable and sporty.
Nothing looks worse on your feet than a dirty pair of dress shoes—especially if you have somewhere important to be. You don’t want to show up to the wedding (or even to work, really) with a scruffy pair. If you see some dirt or staining, it’s best to take care of it immediately—or risk long-term damage.
“It’s important to not let dirt sit on the shoes,” says Jesper Ingevaldsson, who leads the iconic shoe blog Shoegazing. “Not only does it look bad, but it can cause more wear on them. Make sure to brush the shoes off, or wipe them off with a damp cloth if it’s been wet outside, straight after you come home.”
For long term care, Ingevaldsson suggests cleaning products that are specifically made for leather shoes. “Most shoe care brands have good cleaners nowadays that are both relatively gentle and efficient.” He notes that you should cover the whole shoe in the cleaner to avoid water marks—and to let things fully dry before you wear the shoes. “Moist shoes wear out much quicker,” he says.
Ingevaldsson also advises having a few different dress shoes to rotate through, so you’re not wearing the same pair constantly. “Brush or wipe off the shoes when you come home, use shoe trees and occasionally clean and care for your pairs, then they will look better, be better for your feet, and last longer.”
If you want your dress shoes to look clean and classic, rethink how you lace and tie them. “For the lacing, I usually recommend a method that goes by the name ‘Boston two-step’,” says Ingevaldsson, “which has clean straight bars on the front and a relatively even length of the lace parts.”
With the lacing down, you’ve just got to master the knot. Here, you can tie your shoes as you would sneakers, with one caveat: Your knot needs to be horizontal. “There’s basically two types of bows done, even if it may vary on how it’s tied,” says Ingevaldsson, adding that “almost 50 percent of the people use the wrong version.”
“When done wrong, the knot ends up in a vertical position, which looks sloppy, and it un-ties rather easily,” Ingevaldsson says. “When it’s done right, the bow stays in a horizontal position. It’s stronger, since when walking, you pull the knot tighter instead of the other way around. If you notice that you do the bow the wrong way, try pulling the final bow-end the other way around, and it should end up right.”
The proper way to lace your dress shoes, as seen on one of our tester's favorite pairs.
With dress shoes and leather boots, we’ve all been there: the break-in period. It’s the few days of discomfort and blisters that you need to spend with your new goods to make them fit just perfectly. “If you buy good-quality dress shoes, there’s many layers of leather that needs to soften up and conform to your feet before the shoes are really comfortable,” says Ingevaldsson.
The good news, according to Ingevaldsson, is that once they’re broken in, nothing will fit you better. “They will become soft and pliable where they should be, at the flex points, while still giving support where they should. Few shoes are as comfortable for a long day of wear as a pair of well broken-in, well fitting pair of dress shoes.”
So how to break them in quickly—and painlessly? There’s not a lot you can do to skip the process, but you can expedite it by consistently wearing your dress shoes when they’re new—including going from the fridge to the couch and back—to get an idea of where your pain points are. “It’s always a good idea to wear dress shoes around the house for a few hours the first couple of wears, so one can loosen up the first bit,” Ingevaldsson says. “Then when you wear them out for the first few times, you can put on blister plasters as a preventive measure in those areas.”
Leather dress shoes, including the best overall pick we chose from Allen Edmonds, require some ... [+] gentle break-in time.
Men's Clothing Shoes It’s also important not to jump head-first into a new pair of dress shoes. “Try not to wear them for full days of walking for the first few outings,” Ingevaldsson says. “The worst thing you can do is buy a pair of new dress shoes just before a wedding and then wear them for a whole day and night of standing, walking and dancing. In a situation like that, the surprise would be if you didn’t get loads of pain.” In other words, plan out your break-in period in advance, and you’ll be good to go.