Allen Edmonds Park Avenue Cap Toe Oxford
Sizes: 5 to 16 | Widths: AAAA to EEE | Colors: 8 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: 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.”
Most Comfortable Dress Shoes For Standing All Day
Elevated Shoe With Cushion And Flexibility
Cole Haan ØriginalGrand Wingtip Oxford
Sizes: 6.5 to 16 | Widths: Medium, wide | Colors: 10 total, including British Tan-Ivory and Blue Marine Nubuck | 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 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.”
Most Comfortable Oxford Dress Shoes
Perforated Leather With Good Airflow And Cushioning
Florsheim Frenzi Perf Toe Oxford
Sizes: 7 to 14 | Widths: Medium (D), wide (3E) | Colors: 3 total, including Tan 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 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.”
Most Comfortable Dress Shoes For Walking All Day
Leather Hybrid That’s Supportive And Grippy
Wolf & Shepherd Crossover Longwing Hybrid
Sizes: 6 to 15 | Widths: Medium | Colors: 7 total, including Maple and Black | 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: 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 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.”
Most Comfortable Formal Dress Shoes
Custom Molds To Your Foot, No Break-In Time Needed
Beckett Simonon Dean Oxford
Sizes: 7 to 14 | Widths: Medium | Colors: 5 total, including Black and Tan | Upper material: 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. 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.”
Most Comfortable Dress Boots
Ergonomic Footbed, Stylish Design
Astorflex Bitflex Chelsea Boot
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 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.”
Most Comfortable Dress Loafers
Slip-On Design, Soft Suede Uppers
Peter Millar Excursionist Penny Loafer
Sizes: 8 to 13 | Widths: Medium | Colors: 3 total, including Sage 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. 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.”
Most Comfortable Affordable Dress Shoes
Cushioned Style For A Modest Price
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. 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.”
Best Of The Rest
Everyone’s dress shoe needs are different, so we selected additional options to consider beyond the pairs we recommend above. While these styles have not been tested, they’ve been thoroughly researched and vetted by our fashion team.
Ankle Boots With Comfortable Soles
J.Crew Kenton Chelsea Boots
Sizes: 7 to 13 | Widths: Medium | Colors: 2 total, including Black and Color Eight | Upper material: Leather | Sole material: Rubber
- What’s notable: This boot features dual pull tabs on the front and back, which makes it easy to pull them on and off.
- What could be better: Color options are limited to black and brown.
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.
Designed To Fit Wide Feet
Anthony Veer Ford Quarter Brogue Oxford
Sizes: 6.5 to 15 | Widths: Medium, wide, extra-wide | Colors: Black | Upper material: Leather | Sole material: Leather and rubber
- What’s notable: This Oxford shoe is available in both wide and extra-wide widths.
- What could be better: Black is the only color option available.
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.
Lace-Ups For On-The-Go
Samuel Hubbard Highlander Plain Toe Derby
Sizes: 7 to 14 | Widths: Medium (D), wide (EE), extra-wide (4E) | Colors: 3 total, including Navy and Black| Upper material: Leather | Sole material: Vibram rubber
- What’s notable: These shoes come in wide and extra-wide widths, and they’re compatible with orthopedic inserts.
- What could be better: The nubuck style isn’t fully water-resistant, so you may want to treat the uppers before walking in wet conditions.
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 Derby shoes 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.
Casual-But-Transformational Dress Shoe
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 have a padded tongue and removable foam insole with extra cushioning as well as a shock-absorbent midsole. The elastic laces allow you to get a customizable fit, and the rounded toe allows movement and breathing room. Style tip: The black and navy shades read dressier than the lighter shades.
- This story was written by Forbes Vetted contributing writer and editor Molly Calhoun, who’s covered dozens of stories for our fashion vertical.
- 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 iconic shoe blog Shoegazing.
- The publishing of this article was overseen by deputy editor Kari Molvar, a fashion industry veteran with over two decades of experience covering men’s and women’s apparel.
- We regularly update this article to ensure all selections continue to meet the criteria for their respective categories. In May 2024, fashion writer Claire Epting reevaluated each pick and named the Amberjack Original as our best overall pick.
How We Chose The Best Men’s Comfortable Dress Shoes
To determine the most comfortable dress shoes for men, we considered 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.
- We enlisted the critical opinion of Forbes Vetted global accounts manager Matt Flood, who tested our top picks over a period of a few weeks, taking notes on the pros and cons of each.
- We pored over dozens of customer reviews to learn more about how each pick has performed with a wide range of shoppers.
Our tester wore each pair of shoes, evaluating everything from comfort to weight to sizing.
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.
“It’s important to remember that you have a foot shape, not just a shoe size,” says foot expert Colin Dombroski. “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, 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.
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.
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.”
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.
Who Makes The Most Comfortable Men’s Dress Shoes?
Our top picks cater to different needs. 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 Are The Best Men’s Dress Shoes For Standing 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, 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.
How Should I Clean My Dress Shoes?
“It’s important to not let dirt sit on the shoes,” says Jesper Ingevaldsson, who leads the iconic shoe blog Shoegazing. “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. 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.
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.
Leather dress shoes, including the best overall pick we chose from Allen Edmonds, require some gentle break-in time.
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.” 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. Plan out your break-in period in advance, and you’ll be good to go.
