The wrong pair of dress shoes can be stiff and painful. The right dress shoes, on the other hand, mold to your feet and feel great all day. After speaking to footwear experts and testing multiple pairs, we named the Amberjack Original the most comfortable dress shoes for men: They’re designed with supportive heat-activated midsoles and a perforated sheepskin lining that promotes airflow. If you’re going to be standing for long periods of time, we also recommend the Cole Haan ØriginalGrand Wingtip Oxfords, which have flexible, sneaker-like soles that support your feet for hours on end.
Based on extensive testing and expert advice, we found the ten most comfortable dress shoes for men.
Illustration: Forbes / Photo: Retailers
To determine our top picks, we had our in-house tester, Forbes Vetted group project manager Matt Flood, wear ten pairs of dress shoes over the course of a few weeks. In addition to sharing his overall impression of each shoe, he assessed each one’s flexibility, arch support, breathability and fit. Ahead, you’ll find which pairs scored the highest marks, along with expert advice from three footwear specialists on the most comfortable dress shoes for men.
Most Comfortable Dress Shoes Overall: Amberjack The Original
Most Comfortable Leather Dress Shoes: Allen Edmonds Park Avenue Cap Toe Oxford
Most Comfortable Slip-On Dress Shoes: Peter Millar Drift V2 Sneaker
Most Comfortable Dress Shoes For Standing All Day: Cole Haan ØriginalGrand Wingtip Oxford
Most Comfortable Dress Loafers: Peter Millar Excursionist Penny Loafer
Most Comfortable Oxford Dress Shoes: Florsheim Frenzi Perf Toe Oxford
Most Comfortable Dress Shoes For Walking All Day: Wolf & Shepherd Crossover Longwing Hybrid
Most Comfortable Formal Dress Shoes: Beckett Simonon Dean Oxford
Most Comfortable Dress Boots: Astorflex Bitflex Chelsea Boot
Sizes: 7 to 15 | Widths: Standard, wide | Colors: 13 total, including Honey and Obsidian | Upper material: Full-grain leather | Sole material: Rubber
What’s notable: Amberjack’s dress shoes feature athletic outsoles and heat-activated insoles that mold to your foot.
What could be better: According to several reviews, these shoes are on the heavier side.
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 rubber outsole that provides plenty of traction on uneven surfaces. The shoes also feature a sheepskin lining that’s perforated to encourage air flow (you can even wear these shoes without socks if you prefer). “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,” says Flood.
In addition to leather, this pair also comes in suede—and beyond the usual brown and black, you’ll find shades of gray, navy blue and taupe. While the sneakers run true to size, the brand recommends sizing down if you’re between sizes.
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Sizes: 5 to 16 | Widths: AAAA to EEE | Colors: 9 total, including Black and Walnut | Upper material: Calfskin | Sole material: Leather
What’s notable: This shoe comes in 10 width options so everyone can find a pair that fits them just right.
What could be better: The leather material requires a decent amount of break-in time.
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. The single-layer leather sole gives the shoe a low profile; meanwhile, the leather-lined interior and cork insoles mold to your foot for optimal comfort. “You can tell these things are made well,” says Flood. “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.” Another notable feature: This shoe is available in 10 different widths, so you can find the size that’s just right for your feet.
WHAT WE UPDATED
In the October 2024 update, we added tester feedback for the Peter Millar Drift V2 Sneaker and provided more information for what to consider when shopping for dress shoes.
We refreshed the specs for each of our recommendations and added the Peter Millar Drift V2 Sneaker as our pick for the most comfortable slip-on dress shoes.
Peter Millar
Peter Millar Drift V2 Sneaker
Sizes: 8 to 15 | Widths: Medium | Colors: 4 total, including Gale Grey and Ivory | Upper material: Textile | Sole material: Rubber
What’s notable: These business-causal sneakers from Peter Millar have a breathable textile upper that keeps feet ventilated and cool.
What could be better: The lighter colors easily show dirt and stains.
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. Their textile mesh upper is supportive and breathable. They also have a padded tongue and removable foam insole with extra cushioning, as well as a shock-absorbent midsole. “These shoes are very comfortable,” says Flood. “The uppers remind me of Nike flyknit material, making them easy to put on and fit well to your foot. The sole has a good amount of squish and solid construction for a non-leather shoe. They have been holding up well, and I’ve worn them for a few weeks in total.”
Also great: The elastic laces allow you to easily slip the shoe on and off, while the rounded toe allows movement and breathing room. Style tip: The black and navy shades read dressier than the lighter shades.
Sizes: 6.5 to 16 | Widths: Medium, wide | Colors: 10 total, including British Tan/Ivory and Black Leather/White | Upper material: Leather, textile | Sole material: Rubber
What’s notable: A lightweight, flexible sole makes these shoes comfortable straight out of the box.
What could be better: Some customers note that they scuff up easily, so they may not look new for very long.
Cole Haan is at the top of foot specialists’ lists for comfort, and this pair is our dress shoe pick on our list of the best shoes for standing all day. 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 and foot-friendly flexibility, and they’re lightweight yet supportive. “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,” says Flood. Another bonus: These offer a great fit and comfort right out of the box. They’re also available in a wide width if you need a little extra room.
Sizes: 8 to 13 | Widths: Medium | Colors: 3 total, including Pebble and Chestnut | Upper material: Suede | Sole material: Leather and rubber
What’s notable: Water-resistant suede and durable rubber outsoles make these loafers a great choice for grassy terrains.
What could be better: They run on the larger side, so finding your right size might take some trial and error.
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. (We also found it worthy of inclusion as the top suede pick on our list of the best loafers for men.) It’s made from supple water-resistant suede with hand-stitched detailing, resulting in a polished look that doesn’t feel too stuffy. “These penny loafers are a great warm weather or summer option,” says Flood. “I like how easy it is to get them on and off without having to tie them.”
A lightweight EVA outsole allows you to stand on your feet for hours without soreness. If you want a stylish and comfortable loafer, this is the way to go—just keep in mind that these shoes won’t look as formal as a traditional lace-up style. Our tester notes that this style runs a little big, so size down a half-size if you want a sock-like fit.
Florsheim
Florsheim Frenzi Perf Toe Oxford
Sizes: 7 to 14 | Widths: Medium (D), wide (3E) | Colors: 3 total, including Gray and Navy | Upper material: Leather | Sole material: Rubber
What’s notable: This dress shoe from Florsheim features a perforated upper that keeps your foot ventilated throughout the day.
What could be better: Due to its wider-than-average toe box, it’s easy to order one size too large.
Florsheim is well-respected for its high-quality men’s shoes. The Frenzi Perf Oxford has a cushioned insole and a flexible outsole that provide a comfortable fit for all-day wear. “I like the breathability of the Frenzi, and the toe box is a little wider than some of the other options I tested,” says Flood. The design is classic and stylish, so you can dress this shoe up or down—however, the white outsole skews a little more casual than formal. Just keep in mind that these shoes are made of nubuck leather, which 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.
Sizes: 6 to 15 | Widths: Medium | Colors: 5 total, including Maple and Black | Upper material: Calfskin leather | Sole material: Rubber
What’s notable: This dress shoe from Florsheim features a perforated upper that keeps your foot ventilated throughout the day.
What could be better: It has a wider-than-average toe box, which makes finding your correct size a bit tricky.
The Crossover is a good choice for guys looking for a shoe that can be worn for both work and casual occasions. The shoe has an athletic TPU sole that allows you to walk long distances easily and a removable memory foam footbed for a plush feel. The outsole provides plenty of traction to keep you feeling stable on different kinds of terrain. “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,” says Flood. The clean aesthetic also makes it easy to pair with anything in your wardrobe. What’s more, the interior has a chafe-free lining, and the outer calfskin leather has been treated to improve softness, which cuts down on the break-in time.
Sizes: 7 to 14 | Widths: Medium | Colors: 5 total, including Black and Tan | Upper material: Full-grain leather | Sole material: Leather, rubber
What’s notable: These Oxford shoes from Beckett Simonon have a tapered footbed for optimal arch support.
What could be better: Some reviewers say they cause blisters during the break-in period.
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. “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,” says Flood. “I think they have the best construction out of all the shoes I tried.” For added stability, a steel shank is riveted to the insole and outsole. The entire shoe is crafted from full-grain leather that’s durable yet soft and smooth, right out of the box. Another bonus: The Vachetta leather lining absorbs sweat and controls odors.
Sizes: 7 to 15 | Widths: Medium | Colors: 5 total, including Stone and Dark Chestnut | Upper material: Leather | Sole material: Rubber
What’s notable: This sleek boot has a natural crepe rubber sole that’s both eco-friendly and incredibly comfortable.
What could be better: Crepe rubber isn’t known for its durability, so these boots won’t have the same longevity as those made with synthetic rubber.
Astorflex’s top-rated Chelsea boots caught our attention when we were evaluating the best dress boots for men, where they’re featured as our pick for the best Chelsea dress boots. They’re made with high-quality beeswax nubuck leather from Europe, which only gets better-looking with age. The boot has an ergonomic footbed and 100% natural crepe rubber sole that’s soft and comfortable. “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,” says Flood.
You can also feel confident that you’re getting a high-quality product: 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.
Macy’s
Johnston & Murphy Lewis Plain Toe
Sizes: 8 to 14 | Widths: Medium (D) | Colors: 2 total, including Tan and Black | Upper material: Full grain leather | Sole material: Leather and rubber
What’s notable: A memory foam insole provides ample cushioning, making this shoe comfortable enough for all-day wear.
What could be better: The leather quality isn’t as high as the pricier options on this list.
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. “This is a nice, simple option for a comfortable dress shoe,” says Flood. “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.” While this option 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.
Why Trust Forbes Vetted
The Forbes Vetted team has researched, written and published a wide catalog of footwear stories, including shopping guides on the best dress sneakers for men and the best walking shoes for men.
This story was written by Forbes Vetted contributing writer and editor Molly Calhoun, who’s covered dozens of stories for our fashion category.
Calhoun spoke with three foot and footwear specialists: Colin Dombroski, PhD, founder and clinical director at orthotic and footwear company SoleScience; Howard Friedman, DPM, podiatrist and owner of Suffern Podiatry; and Jesper Ingevaldsson, founder of the well-known shoe blog Shoegazing.
Leather dress shoes, including the best overall pick we chose from Allen Edmonds, require some … [+] gentle break-in time.
Alyssa Flood Photography For Forbes Vetted
The publishing of this article was overseen by deputy editor Kari Molvar, an industry veteran with more than two decades of experience covering lifestyle topics, and most recently, men’s and women’s apparel.
We regularly update this article to ensure all selections continue to meet the criteria for their respective categories. It was last updated in October 2024.
How We Chose The Best Men’s Comfortable Dress Shoes
To determine the most comfortable dress shoes for men, we looked at specifications such as size and width availability, adjustability, cushioning and flexibility.
We considered shoes highly recommended by podiatrists and evaluated the models highlighted by the experts we spoke with. Specifically, Friedman recommends the Johnston & Murphy Lewis Plain Toe for its wider-than-average fit.
We enlisted the critical opinion of Forbes Vetted global accounts manager Matt Flood, who tested nine pairs over the course of a few weeks. Flood evaluated each shoe’s breathability, fit, weight and wear, making notes of what stood out and what could be better.
Our tester wore each pair of shoes, evaluating everything from comfort to weight to sizing.
Alyssa Flood Photography For Forbes Vetted
We pored over dozens of customer reviews to learn more about how each pick has performed with a wide range of shoppers. All of our selections have an average customer rating of at least 4 out of 5 stars.
What To Consider About The Most Comfortable Dress Shoes For Men
When shopping for comfortable dress shoes, you should consider the shoe’s fit, shape, sole materials and more. Here are our expert-backed tips for finding the right pair.
Fit
“It’s important to remember that you have a foot shape, not just a shoe size,” says Colin Dombroski, PhD, founder and clinical director at orthotic and footwear company SoleScience. “You may measure a certain size, but that size is only a starting point of your length, width and depth.” 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. Friedman adds that 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,” he says.
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, find a style that can accommodate you. In general, a rounded toe is 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.”
Our tester appreciated how Beckett Simonon’s dress shoes come with a dust bag and removable insoles … [+] to add extra comfort.
Alyssa Flood Photography For Forbes Vetted
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. 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.”
Upper Material
The “upper” refers to the part of the shoe that covers your foot, and they often have laces or straps to offer a more secure fit. Dress shoe uppers can be made from various materials, from leather to knit fabric to canvas. Most options are crafted from leather or suede because these materials are durable, comfortable and look polished. Leather has a smooth surface and tends to be more durable than suede, which has a soft and supple feel. (Leather comes from the outer layer of the hide, which is exposed to the elements and becomes tough as a result.) While the best materials for your shoes come down to personal preference and lifestyle, leather is an excellent option for most shoppers, and it ages well and can be used for many years.
Lace-Up Vs. Slip-On
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.
Alyssa Flood Photography For Forbes Vetted
Frequently Asked Questions (FAQs)
What Brand Is Known For Making Comfortable Footwear?
If you prioritize overall comfort and versatility, the Amberjack Original 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 Allen Edmonds Park Avenue Cap Toe Oxford. This pair is known for its quality leather and variety of width options, offering both comfort and durability.
What Is The Most Comfortable Shoe To Wear All Day?
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, 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.
How Can You Tell If Dress Shoes Are High Quality?
High-quality dress shoes have uppers that are made of genuine leather, suede or fabric that’s been either stitched or securely glued to the sole. Shoes specifically made of full-grain leather (like the Johnston & Murphy Lewis Plain Toe) are particularly premium. Stitching should be even, with no fraying along the edges, the sole should feel thick and durable and the inside of the shoe should be smooth.
How Do I Stop My Dress Shoes From Hurting?
With dress shoes and leather boots, we’ve all experienced 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 Jesper Ingevaldsson, who leads the iconic shoe blog Shoegazing.
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.” To keep pain to a minimum, it’s 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. Plan out your break-in period in advance, and you’ll be good to go.
