Once upon a time, around when Steinbeck penned “Of Mice and Men,” the American dream was to own a piece of land. Today, with these interest rates (jeez), that sounds more like a pipe dream. Instead, for some, the American dream is having their cake and eating it too — in this case, finding handsome but also comfortable dress shoes for men.
While finding such a shoe might also sound like a pipe dream, we’re here to tell you that it’s absolutely possible. In fact, as an editor who also worked in the shoe industry for nearly 10 years, it’s a pleasure to tell you that having both comfort and style in a dress shoe is easily attainable if you know what to look for.
In this review, we’re going to examine those variables from brand to brand, touch on how to measure shoe size properly, and dive into some comfortable dress shoes that are most likely to work for any man with feet.
What Are the Most Comfortable Dress Shoes?
This is an easy question to ask, but one that is extremely complex. Long story short, the answer lies within the composition of your feet. The most comfortable dress shoes are going to be different for wide feet compared to feet that are narrow or flat. Aside from composition, personal style absolutely still factors into this equation.
“Then how the heck are you going to review the most comfortable dress shoes and tell us that it’s accurate?” That’s fair, but we knew you’d ask that.
For our testing, we wore a combination of 15 of today’s best-rated dress shoes from online as well as the shoes that get returned the least based on conversations with in-store salespeople. We looked for styles that offered overs and unders sizing as well as multiple widths, soft leathers, and shock-absorbency if possible.
In addition to that, yours truly has been lucky enough to test somewhere on the higher side of 100 different pairs of men’s dress shoes since 2009 thanks to various occupations and running a men’s blog. Our research on trends, coupled with personal expertise and an eye for what stays in style through the years, is how we know we’ve picked the best options.
But none of this means anything unless you know your actual shoe size.
How to Measure Shoe Size
You don’t have to buy a Brannock device, but you do need to use one to find your correct shoe size.
These devices, which you’ve probably seen before, are the industry standard for accurate sizing. Luckily, most shoe stores will have one readily available and salespeople will more than likely help get you measured. This measurement is more accurate when you stand up straight, so definitely find assistance when measuring.
Here’s how to measure shoe size:
- Heel-to-Toe: With some help, place your heel on the device, left or right as it’s labeled, and stand up straight, distributing your weight evenly to get the heel-to-length measurement.
- Arch Length: Whoever is helping you will then slide the arch length tool (it’s on the inside of the foot) north-to-south to line it up with the ball of your foot. Compare this measurement with that of the heel-toe and size up to the larger number or take the average if they’re really close.
- The Width: From there, slide the width bar (outside of the foot) east-to-west until it’s flush with the boundary of your foot. Match the numeric size with the corresponding letter size to find your foot’s width. A medium width, with which most shoes are designed, is a “D” on this device.
In the world of foot composition, most people tend to have feet of a similar shape. The average men’s shoe size in the United States is around 10-10.5D. However, brands that make the most comfortable dress shoes for men understand that not all guys have average-sized feet and, wisely, include overs and unders sizing as well as narrow and wide widths to fit all feet.
For this review, it’s important to know that SPY Reviews Editor, Anthony Mastracci, who performed the majority of our testing, has feet that are a very average 10.5D without any problem areas. With that considered, here are the most comfortable dress shoes we’ve found to fit feet of all types.
|Available Sizes||US men’s 7-16|
|Available Widths||Medium, wide|
|Sole Material||Full EVA|
10 years ago, Cole Haan released a shoe called the LunarGrand. This was a dress shoe that combined the cushioned sole of a running sneaker from Nike, who owned the company at the time, with a traditional longwing dress shoe. 9-to-5ers across the country flipped out, and soon after, we saw guys in the Financial District rocking traditional navy suits with these shoes that had electric orange foam soles. Wondering what the heck was going on, in 2014, we tried some for ourselves and were instantly hooked on these comfortable dress shoes.
Today, in a post-Nike era, Cole Haan continues to make the OriginalGrand — the new name of (essentially) the same shoe. We’ve seen countless iterations of this icon, including the ever-flexible Cole Haan ZeroGrand, but many fans remain loyal to the OG (literally), arguably the first really good dress sneaker that men could get away with as office attire.
Nearly a decade after first trying this style, the OriginalGrand remains one of the most comfortable dress shoes we’ve ever worn and was also named SPY’s Most Comfortable Dress Shoe of 2022 as part of our Best of 2022 Awards. We love the soft leather on top of the EVA sole and appreciate that we have something both comfortable and cool looking, in the longwing style, to wear both dressed up and casually. It’s an arch’s dream come true, with its astounding malleable and shock-absorbent insole, and it barely weighs anything.
One stride we’re proud to see Cole Haan take, to which they publicly committed during their recent collaboration with Pendleton, is the desire to focus on sustainability from materials to supply chain and manufacturing. The brand is already part of the Leather Working Group but has now introduced the “Flower Foam” sole, a proprietary material designed with at least 25% natural dandelion rubber or recycled materials by weight.
Furthermore, for those tough-to-fit feet, the OriginalGrand is available in overs and unders sizing as well as medium and wide widths. All of this for under $200 is a no-brainer — get brown and then also something funky.
- Denim and suit-friendly
- All-day comfort
- Zero break-in time
- Great variety
- Sustainable materials
- Good leather, but could be of higher quality
- Sole “deflates” after many wears
- Kind of bulky
Allen Edmonds Park Avenue Cap-Toe Oxford
Best For: Guys with suit-centric jobs who want a reliable, but understated, comfortable dress shoe.
Why We Chose It: Some might argue, but this is probably the most iconic men’s dress shoe from one of the most iconic American shoemakers in the game.
|Available Sizes||US men’s 5-16|
|Available Widths||AAAA, AAA, AA, A, B, C, D, E, EE, EEE|
|Made In||United States|
|Sole Material||Leather with rubber block heel|
For those who have never worn a pair of Allen Edmonds dress shoes before, you might wonder how they could possibly provide comfort with insoles as hard as theirs. In reality, when you consider some of the best shoe insoles, you’ll find that they’re quite firm. That’s because a firm, but contoured footbed does wonders for preserving the arch of a foot. In the case of the Allen Edmonds Park Avenue, under the leather insole is a layer of their CustomCork technology, which molds to the contours of the wearer’s foot over time. The result is a semi-custom fit insole that provides long-lasting comfort.
That’s exactly what we’ve found wearing this classic Allen Edmonds style. Truthfully, we’ve been rotating the same pair of Park Avenue Cap-toe shoes for five years. At this point, the footbed is completely molded to the bottom of our foot and they’re good to keep our feet happy through a whole day of work, including that tiresome trip back home.
What we love most about the Allen Edmonds Park Avenue is that they feel like an heirloom. In addition to being comfortable dress shoes, they’re masterfully constructed in Wisconsin with European calfskin leather. After a while, you can easily have this shoe resoled with leather or rubber. They feel durable when you touch them and it’s clear that they’re built to last, which is great because the style is timeless. Wear these with your suit to the office or a pair of jeans and a classic sweater for Casual Friday.
In our testing, the Park Avenue dress shoes picked up the most points in our specs rankings. Considering comfort for all, this shoe earned 102 points out of 100, which has never happened before. We awarded bonus points for the Park Ave’s immense size range, from a men’s size 5-16, and unheard-of width offerings, ranging from AAAA-EEE, from narrowest to widest, again, D meaning “medium.”
- Industry-leading size offerings
- Made in U.S.
- Classic style
- Hardy construction
- Molding insole
- Lacks shock absorbency
- Expensive, but worth it
|Available Sizes||US men’s 8-13|
|Sole Material||Full EVA|
Perhaps what came as the biggest surprise in our quest for the most comfortable dress shoes was this new addition to the legendary Johnston & Murphy brand — the Jameson Longwing. This shoe is handcrafted in Italy with Italian leather and built on a split-leather welt. It also boasts an EVA sole and the brand’s XL Extralight technology. After wearing these dress shoes, to us, they embody the refinement that the Cole Haan OriginalGrand lacks.
While sneaker-soles make for very comfortable dress shoes, they tend to bring a certain bulkiness that detracts from traditional officewear. With the Johnston & Murphy Jameson Longwing, you can have a dress shoe with a sneaker sole that was designed to look sleek. The toe is slightly more tapered than a classic round toe, visually elongating the shoe just a pinch. The leather is clearly of a higher quality. Additionally, the sole is slightly shorter and less poofy, making it look slimmer. We’re calling the looks a win, but are they comfortable?
Aside from the OriginalGrand, the Jameson Longwing was the only other style to ace our comfort testing across all categories. They were comfortable right out of the box in our regular size and required no breaking in other than the molding of the insole. The EVA outsole, despite being slimmer, is still thick enough to handle rocks, cobblestones, and other obstacles without feeling them. We would have loved to see these shoes offered in a wide as well as overs and unders sizing to extend their comfort to more guys.
As for the price tag, on the date of publishing, these shoes sit at $275. While that sounds like a lot, hear us out on this one. Even though the sole is a lesser expensive material, these shoes are still Italian-made, and at under $300, that’s an incredible introductory price point. Grab a simple pair of dress socks and you’re pretty much office-ready.
- Sneaker, but sleeker
- All-day comfort
- Neutral color palette
- Pricey, but Italian-made
- Welt sole stitching is adequate
|Available Sizes||EU 39-48 (equates to US men’s 5/5.5-14/14.5)|
|Sole Material||Full rubber|
Shoe dogs know that Ecco fans are absolute die-hards, and with good reason — their men’s dress shoes consistently meet expectations year after year. For example, if a man has been wearing the Ecco Helsinki forever and needs a new pair, he can just go get another one and slip into a brand new pair of what he purchased last time. While that’s great, unfortunately, Ecco doesn’t have a reputation for fashion so much as they do for comfort and quality, but that changed recently with a few new product drops including the Citytray Cap Toe Shoe.
The Citytray Cap Toe is a huge upgrade in the style department from Ecco, boasting the brand’s renowned in-house leather, a padded ankle collar, and two types of tech in the sole that strip out some weight while increasing stability.
Wearing the Ecco Citytray Cap Toe dress shoe was a marvelous experience. We got some rain the day we wore it, but thanks to the Ecco Tray rubber outsole, walking wasn’t precarious through the ill-prepared-for-rain streets of Los Angeles. This shoe fit well enough out of the box but was perfectly acclimated by the end of the work day. We were very impressed by the shock absorbency of the insole, which remains a staple of this brand.
This shoe offers a great range of sizes between US 5/5.5 and 14/14.5 with a generously cut width that fits somewhere between medium and wide. If you’re a half size, we recommend sizing down, as Ecco’s European sizing covers, for example, both a 10 and 10.5 simultaneously. And though we’d like to see a larger push for sustainable practices, there’s no denying this is a dependable, comfortable dress shoe that’ll look great with a dress casual or suited look. We wouldn’t be surprised if this took the top spot as your favorite brown cap toe.
- Consistent comfort
- Fashionable design from comfort brand
- Overs and unders sizing
- Four colors available
- Won’t be great for narrow feet
- Lacks sustainability vision
Ace Marks Wingtip Vincent
Best For: Guys looking for a timeless wingtip style that’s sharp and versatile.
Why We Chose It: These Ace Marks wingtips aren’t just comfortable dress shoes, but also an affordable luxury.
|Available Sizes||US men’s 5-18|
|Available Widths||Medium, wide|
|Sole Material||Full leather with rubber heel tap|
Truly affordable luxury goods are hard to find. However, in the last six years or so, we’ve been lucky to have some incredible shoe brands born out of the idea that luxury products can be sold at fair prices with changes to their business model. That’s how we got Ace Marks and their incredible, Italian-made dress shoes at a great price point. They’ve cut out the retail middlemen, preventing extra mark-ups, and the savings go to the customer.
The Vincent wingtip shoe is a classic derby style with stunning broguing details. As far as we’re concerned, this is the epitome of a wingtip dress shoe. This is the type of shoe that instantly makes an outfit look better. After putting them on, truthfully, they also make us want to dress better. But a big part of that stems from the desire to wear them all the time because they’re so comfortable. The Ace Marks Vincent provides all-day comfort after a short break-in period of about 8-10 hours. We found the vamp (on top of the toes) to be shallow, but the entire shoe was surprisingly flexible and overall just a joy to wear.
The comfort and craftsmanship are undeniable, but there’s a trade-off when it comes to direct-to-consumer brands like Ace Marks. It’s not terrible, but sometimes, grabbing a pair requires pre-ordering and some patience while they’re manufactured. As of publication, ordering the Vincent wingtip in a size that’s out of stock has an estimated ship date of “March 2023.”
- Incredible value
- Obvious quality
- Iconic style
- Can be resoled
- Can take months for pre-orders to arrive
- Vamp is a bit shallow
|Available Sizes||US men’s 6-16|
|Sole Material||Leather with rubber lugs|
Thursday’s The Saint double monk strap is the best, most comfortable double monk strap we’ve worn in the last five years. These distressed, lug-sole dress shoes came as a surprise because, as lovely looking as monk strap shoes are, they’re easily the least comfortable type of dress shoe to wear. Oftentimes, because of the belted closure mechanism, pressure is distributed to different areas of the foot that most guys aren’t used to enduring, which can lead to blisters and scratches around the ankle.
This shoe, however, wears as beautifully as it looks. The Saint kept our feet happy at work through a nine-hour day, including our commute, during which the lug sole played a big role in stabilization. The break-in period was shorter than most other similar dress shoes, warming up and molding nicely by the end of the day thanks to the soft (but very high-quality) leather. We found the sizing to be a little generous, running about a quarter-size large, but not enough to warrant changing sizes. If your foot is narrow, you may prefer a half-size down. Despite that, there was no experience of rubbing or scratching that typically comes with shoes that are too big.
When we got home and took these off, we noticed that the leather insole in one of the shoes had become unglued and shriveled up a little bit. This is most likely due to slight movement inside the shoe due to big sizing, but thankfully, it’s an easy fix at the cobbler or even at home with some shoe glue. Even though we couldn’t feel anything happening under our feet, it’s still something we need to fix before the next wear, but make no mistake — there will be a next time.
- Incredibly stylish, unique
- High-quality leather
- Great price for this craftsmanship
- Works with LWG-Certified tanneries
- Runs big — consider before buying
- Possibly not enough glue under insole
Florsheim Sorrento Wingtip Oxford
Best For: Guys shopping for comfortable dress shoes within a budget.
Why We Chose It: Most budget dress shoes are lacking across numerous categories but the Sorrento’s design is sharp as a tack, feels wonderful, and offers sizing and color options.
|Available Sizes||US men’s 7-14|
|Available Widths||Medium, wide|
|Sole Material||Full rubber|
Here’s a fact for you: The Florsheim shoe company has survived the Great Depression, a handful of wars, and more recently, COVID-19. Since 1892 (incredible), Florsheim has been a staple in men’s dress shoes. And while over the years manufacturing processes have changed, as well as the American outlook on style, their commitment to providing a quality pair of comfortable dress shoes for men is unwavering.
The Florsheim Sorrento Wingtip Oxford is a continuative, all-the-time style that every guy needs in his wardrobe. Despite the incredibly affordable price, the Sorrento doesn’t sacrifice aesthetics to bring the cost down, as many budget brands do. In fact, its silhouette is nearly identical to a popular Magnanni style that’s over three times as expensive.
Looks aside, this shoe feels great throughout the workday thanks to its soft leather and cushioned footbed. In our 10.5D size, we did find it to be a hair on the narrow side because of the tapered toe, but not enough to warrant sizing up or needing a wide. At the end of the day, the leather warms up from body heat and molds around the outer bones of the foot.
If there’s one wish we had, it’d be for a thicker rubber outsole. With that said, the shoe is completely resoleable by a good cobbler.
- Carbon neutral shipping
- Sorrento shape available in other styles
- Sleek as hell
- Thin leather and outsole
- Leather more prone to creasing
|Available Sizes||US men’s 7-14|
|Sole Material||Leather with rubber block heel|
Beckett Simonon is another direct-to-consumer brand, similar to Ace Marks and their business model, that brings customers incredible value for top-tier footwear by skipping the middleman. But that doesn’t mean they also cut corners on quality, in fact, quite the opposite. Hand-crafted in Colombia, each Beckett Simonon shoe is made-to-order, including their Beaumont Loafer, which we tested for this review. Making shoes made-to-order helps significantly reduce their overall carbon footprint by running a lean operation with less waste.
The Beaumont Loafer by Beckett Simonon is, for us, one of the two best loafers a man could own, right next to a classic penny loafer. We love wearing this tan horse-bit loafer throughout the year as the perfect accent shoe for suiting or with jeans, and sometimes even with nicer shorts. It’s made from full-grain calf leather that’s sourced from a Leather Working Group Gold-Rated Italian tannery, which is very impressive from a sustainability standpoint.
But we’re talking about comfortable dress shoes here, not just looks. The Beaumont Loafer was very easy to wear throughout the day. These horse-bit loafers scored bonus points with their moccasin design, which allowed the bones on the side of our feet to create a custom imprint in the leather that helped negate any width issues and kept the toes comfortable. Though we desired a bit more shock absorbency under the forefoot toward the tail end of the day, the entire top side of the shoe, including the ankle collar, was extremely comfortable.
Don’t forget to wear these with your favorite pair of no-show socks.
- Available in five colors
- Padded ankle
- Can take over three months to ship
- Desired more padded insole
- Horsebit jangles loudly
|Available Sizes||US men’s 7-13|
We’ve only seen a handful of brands try to beat sneaker sole industry leader, Cole Haan, at their own game. But with Amberjack, we’ve got our popcorn out and we’re ready to watch. A newer face in the market, Amberjack’s focus is on combining proprietary and premium materials that are ethically manufactured and result in a high-quality, comfortable dress shoe. Well, we tried The Original in the Honey Suede and it moved us enough to call it the best dress sneaker of 2022. Not only that, but it earned a SPY Best of 2022 Award as the Best Office Sneaker.
We loved wearing Amberjack’s The Original dress shoe because it felt like walking on clouds thanks to a heat-activated insole with an incredible arch. But their comfort doesn’t just lie inside — they’ve taken the time to design a shoe around, what we’d consider, common customer complaints. For example, their ankle collar and tongue are both padded, they’ve included perforations across the vamp for ventilation, and the width is cut generously for a little extra pinky toe wiggle room.
What we were most impressed by with The Original was their proprietary TPU outsole. Made in Portugal, The Original’s outsole consists of two sections — an athletic “crash pad” under the forefoot and a dense rubber plate through the shank and heel. Together, these two provide a little extra spring in the push-off as well as extra stability and shock absorbency during the landing in a natural walking stride — it’s like buttah.
- High sustainability focus
- Premium materials
- Nearly perfect out of the box
- May not work for narrow feet
- Extremely round toe, almost snub
- Lacks sex appeal
How We Determined the Most Comfortable Dress Shoes
For two months, we were the best dressed in the office as we tested out several hands full of dress shoes. Were they all comfortable? No. But many of them were in fact comfortable dress shoes, which made our lives a lot easier. And even though we have next to no space left in our apartments because we can’t fathom giving any of them away, it’s worth it to figure this out for feet everywhere.
Now, one thing is for sure — everyone’s feet are different. We know this, but we had to start somewhere, and that was with a reviewer whose feet are medically sound and very average in size, in the best way possible. From there we considered the following to paint a better picture for the masses:
Sizing & Availability — Sizing means everything when trying to perfectly fit feet. The most comfortable dress shoes were more accommodative, and we scored higher for styles that offered overs and unders sizing as well as different widths.
All-Day Comfort — This goes without saying but the shoes we tested needed to be comfortable through the workday. We considered technical design here as well and scored higher based on how our feet felt at the end of the day.
Break-In Period — Shoes should NOT have to be “broken in,” but there is a short period during which cold leather has to warm up and mold. For shoes that made this process easy, we scored higher.
Materials & Craftsmanship — Some of the most comfortable dress shoes feel good because of their good materials. We scored higher for premium and technologically advanced materials as well as craftsmanship designed to promote happy feet.
Style — We know this has less to do with comfort, but you should be able to have your cake and eat it too. We gave an edge to styles that provided both comfort as well as cool style.
Why Trust SPY When Shopping for Comfortable Dress Shoes
Here at SPY, we definitely have a problem with, or rather, a proclivity for, finding too many awesome shoes. Shoes are the second thing we look at when meeting new people and the first thing we look for when shopping a sale, so we were very excited to find some comfortable dress shoes for SPY readers.
Additionally, SPY Reviews Editor, Anthony Mastracci, who contributed to this article, carries nearly 10 years of experience in the shoe industry and as a menswear blogger. In this time, he’s been fortunate enough to have tested close to 100 pairs of dress shoes. This article includes some of his long-time favorites as well as some that recently impressed him.
Other than shoes, SPY is all up in the men’s style space, having tested a growing number of categories. Recently, we’ve reviewed the best white t-shirts for men, the best moisture wicking shirts, and even the best underwear.
If you’re interested, you can read more about How We Test Products at SPY.
About the Author: Anthony Mastracci
SPY Reviews Editor, Anthony Mastracci, is a Los Angeles transplant by way of Boston. A bearded style guy, Anthony enjoys helping guys look and feel their best through outfit coordination and recommending top-tier grooming products.
Recently, Anthony has written about the new men’s grooming brand, ATWATER skincare, and shared his favorite sneaker purchase of the year as well as his go-to brand for men’s joggers. Otherwise, you can find him on Instagram looking flashy.