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 look sleek and stylish—and also come with extra padding and ... [+]
To select our picks, our in-house 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 shoes. And for more fashion advice, check out our guides to the best men’s dress shirts and best men’s jeans.
- Most Comfortable Dress Shoes Overall: Allen Edmonds Park Avenue Cap Toe Oxford
- Most Comfortable Leather Dress Shoes: Amberjack The Original
- Most Comfortable Dress Shoes For Standing All Day: Cole Haan ØriginalGrand Wingtip Oxford
- Most Comfortable Oxford Dress Shoes: Florsheim Frenzi Perf Toe Oxford
- Most Comfortable Dress Shoes For Walking All Day: Wolf & Shepherd Crossover Longwing
- Most Comfortable Formal Dress Shoes: Beckett Simonon Dean Oxfords
- Most Comfortable Dress Boots: Astorflex Bitflex Chelsea Boot
- Most Comfortable Dress Loafers: Peter Millar Excursionist Penny Loafer
- Most Affordable Comfortable Dress Shoes: Johnston & Murphy Lewis Plain Toe
The 2024 Forbes Vetted Best Product Awards are here: Explore our 150 top-recommended items across categories after extensive research and testing.
Best Of The Rest
Everyone’s dress shoe needs are different. With that in mind, we selected additional options to consider, if you’re looking for other pairs beyond what we recommend above. All of the dress shoes here have been vetted by our fashion team.
Why Trust Forbes Vetted
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.
How We Chose The Best Men’s Comfortable Dress Shoes
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.
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 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:
- 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.”
Our tester appreciated how Beckett Simonon's dress shoes come with a dust bag and removable insoles ... [+]
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 ... [+]
How Should I Clean My Dress Shoes?
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.”
What’s The Best Way To Tie Dress Shoes?
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.
Do I Need To Break In Dress Shoes?
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 ... [+]
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.
Comparison Guide For Men’s Dress Shoes
Our top picks cater to different needs. If you prioritize overall comfort and versatility, the Allen Edmonds Park Avenue Cap Toe Oxford is your best bet. It's a classic design that provides a good balance between style and support, making it suitable for work, weddings or dressier occasions. Another contender in this category is the Beckett Simonon Dean Oxfords. This pair is known for its quality leather and handmade construction, offering both comfort and durability at a slightly more expensive price point.
For those who are on their feet all day, the Cole Haan ØriginalGrand Wingtip Oxford is the way to go. It has a sneaker-like sole that's lightweight and flexible, along with arch support for long hours of wear. If a different style suits your taste, but comfort for extended wear remains a priority, then the Wolf & Shepherd Crossover Longwing is a good alternative. Wolf & Shepherd shoes are known for their memory foam footbed and soft leather, making them a great choice for all-day wear.
Finally, if finding shoes that fit well right out of the box is important, then Astorflex’s Bitflex Chelsea Boot is a solid choice. Chelsea boots are inherently comfortable due to their elasticated sides, and this particular pair is known for its comfortable fit and stylish design. It's a versatile option that can be dressed up or down. Another comfortable Chelsea option is J.Crew’s Kenton boot. It pairs high-quality materials and construction at a reasonable price.
Meet Our Experts
- Colin Dombroski, PhD, is the author of The Plantar Fasciitis Plan: Free Your Feet From Morning Pain and founder and clinical director at orthotic and footwear company SoleScience.
- Turner Allen is a New York-based men’s fashion stylist, and the founder and lead stylist at Style Turner.
- Howard Friedman, DPM, is a podiatrist and board-certified by the American Board of Foot and Ankle Surgery. He is the founder of Suffern Podiatry in Suffern, New York, and is well versed in comfortable footwear for active patients, having completed 5 half-marathons and several 5-K trail and road races himself.
- Jesper Ingevaldsson is the founder of the iconic shoe blog Shoegazing, which is dedicated to quality shoes made with traditional construction methods. It debuted in 2012 in Swedish—the English version launched 2015—and today Shoegazing is one of the largest blogs in the world about classic shoes.
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