If you really think about it, the casualization of fashion was inevitable.
The more we, as a society, focus on productivity and comfort, the more we realize that the two are inextricably linked.
Silicon Valley entrepreneurs, for example. That ‘I’m-too-busy-innovating to put on a suit and tie’ mentality.
With dress shoes though, you don’t have to sacrifice comfort for style and formality.
This is good news for those of us who still work in suit-and-tie professions, those of you who want to be as comfortable as possible in the few formal events you do attend, and for all of us who don’t want to compromise our adult wardrobe.
Read on to learn about the most comfortable dress shoes on the market today.
Table of Contents
How Did I Come Up With My List?
It’s tough to find shoes that are as formal-looking as they are comfortable. Fortunately, I can confidently say that I’m an expert on the matter.
As far as active research on this goes, I’ve been trying on shoes, scouring reviews on blogs, YouTube, and trade magazines, for a good two weeks. Within that bracket, I’ve looked into well over 50 pairs of shoes.
In the greater scheme of things, I’ve technically been researching this topic for well over a decade.
As a long-time art dealer, I spend as much time running around hard-hat exhibition spaces hanging large paintings as I do having dinners and board meetings with billionaire clients. Basically, I’m one of those suit-and-tie professionals with a physically demanding trade. And I’m not allowed to wear sneakers, ever.
That being the case, I’ve easily tried on well over 100 pairs of dress shoes, actively seeking comfort out as a main priority. Of course, I also consulted colleagues and shoe experts.
The following seven models of dress shoes provide distinct comfort factors, each categorized for specific reasons, starting with the overall best.
7 Most Comfortable Men’s Dress Shoes
My Top Pick: Beckett Simonon Dean Oxford
We’ve spotlit the Deans from Beckett Simonon as a top pick in our Oxfords round-up, and it’s easy to see why. It’s classic, elegantly slim, and made from beautifully waxed, hand-cut full-grain leather. I’ve raved over the brand’s level of hand craftsmanship on several occasions—the soles on the Deans are even hand-sanded.
Since we’ve already highlighted its handsome, versatile style, and its premium build, let me laser focus on how they manage to make it so darn comfortable.
Basically, instead of implementing athletic shoe technology, Beckett Simonon is cleverly strategic in how they use traditional dress shoe materials.
First of all, it’s Blake stitched. I know that in the shoe-loving community, Goodyear-welting is king.
The Blake-stitched Deans, however, are literally immediately comfortable right out of the box. They still have substance to them because of the full-grain leather and the fact there’s stable steel shanks built in. And they do get more comfortable the more you wear them, but you’re not looking at a blister-city break-in process here.
Plus, the Vachetta leather lining naturally manages temperature, and the classy-looking stacked heels are equipped with rubber caps to absorb shock as you walk.
Another plus is that Beckett Simonon, which was originally founded by leather industry veterans, uses a small-batch model that cuts loads of costs. They’re even able to work ethically with the artisans who hand-craft each shoe (check out their website, they even highlight a few of these talented folks).
What I Like
- The combination of the Blake-stitched construction, rubber-capped heels, and Vachetta leather lining provides immediate comfort and natural temperature regulation.
- Regardless of how easy they are to wear out of the box, these shoes are sturdy, built with a steel shank and full-grain leather.
- They have a slim and refined silhouette, flaunting a supple upper and stacked heel, serving up a timeless and adaptable aesthetic.
What I Don’t Like
- As always, though we love a made-to-order model because it allows Beckett Simonon to serve up a $400-value shoe for half the price (and because it’s more artisanal and personal), you may have to deal with irregular wait times. This may mean waiting up to two months for your shoes to arrive.
What Do Other Reviewers Say?
Reviewers love the design and quality, many mentioning that the range of colorways is particularly impressive. There are five options, each neutral and professional, but not without a specific vibe that allows you to accommodate your personal style.
As far as comfort goes, out of the hundreds of reviews I’ve read and watched, a vast majority agree that the Deans are impressively comfortable dress shoes.
Many mention that there isn’t a break-in period (as is the case with me), others mention a non-stressful and quick break-in period, and a few wide-footed gents mention using a shoe stretcher to get to that perfect comfort level.
The Verdict
The Beckett Simonon Deans offer a compelling value proposition, with their hand-crafted full-grain leather construction, good range of colorways, and stylishly tapered silhouette. Details like the stacked heel further take them over the edge.
How comfortable they are make them even more impressive, considering the sturdy frame and steel shank.
Thanks to the resoleable Blake-stitching, shock-absorbing rubber cap, and conforming Vachetta lining, Beckett Simonon manages to build immediately easy-to-wear shoes, using only traditional dress shoe materials and techniques.
The Beckett Simonon Deans are full-grain leather Oxfords that boast a high level of hands-on craftsmanship. At often ~$200, these classic, slim shoes fly miles over their price point. Oh, and they’re also super comfortable, to boot.
Best Budget: Thursday Boots Executive
Not only are the Thursday Boots Executives the best budget dress shoes on our list, they may very well be the most comfortable non-hybrid Oxfords I’ve ever worn.
They’re Goodyear-welted, so they’ll take some breaking in, but once you’re there, we’re talking almost sneaker-like flexibility and support.
The reason why is because Thursday attacks from land, air, and sea, so to speak. They don’t rely on one comfort feature, but multiple components, each of which work together to make each’s contribution that much more effective.
Going down the line, the interior is lined with soft and flexible leather, which is there to conform to your foot.
Beneath that are classic cork midsoles that help the leather create your foot shape, while also providing support. These midsoles work in partnership with shock-absorbing insoles, which are also antimicrobial.
That being the case, these shoes aren’t just ensuring comfort from the wear experience, but hygienically as well.
Once you learn that Thursday came about to strike a balance between comfortable and stylish fashion boots and clunky but strong work boots, it makes sense that they’d eventually get in the dress shoe game with that very same offering.
And again, they do need breaking in because of the Goodyear welt. Still, this combination of strong construction with multi-layered comfort technology ensures these Oxfords will last you years.
What I Like
- Layers of strategic comfort features, from the lithe leather interiors to the cork midsoles and antimicrobial insoles, make these shoes fully engineered for easy wearability and pressure alleviation..
- With a point that’s only moderately sharp and their gradual taper, these shoes can be worn with jeans or a suit..
- The Goodyear-welt construction provides long-lasting sturdiness, easy resoling, and makes these shoes punch way above their price point..
What I Don’t Like
- The Goodyear-welt construction is a pro when it comes to the overall construction, but from a comfort perspective, makes these shoes not immediately wearable the way the Deans are..
What Do Other Reviewers Say?
Comfort aside, reviewers rave about the impeccably hand-waxed full-grain leather, especially since the shoes are also Goodyear-welted. Typically, at this price point, you could get one or the other, so the fact you get both makes the Executives an easy buy.
The Verdict
In addition to being both durably well-built, as well as sophisticatedly comfortable, the Thursday Executives manage to cram a lot of good specs into its sub-$170 price point.
Once broken in, you get the same comfort as cement-soled shoes, but with all of the long-lasting capabilities of its Goodyear-welted architecture.
The Thursday Executives feature a team of comfort-focused features, including the cork midsole and shock absorbing insoles. Uniquely, they’re also Goodyear-welted, perfectly balancing that comfort with a robust, strong build.
Most Comfortable Dress Chelsea: Beckett Simonon Bolton Chelsea
Also hailing from the Beckett Simonon tribe, the Bolton Chelsea Boots combine style, good composition, and a focus on comfort as effectively as the Deans do.
Like his Oxford cousins, the Boltons are built with rich full-grain leather, feature flexible and immediately wearable Blake stitching, and even have SBR rubber heel caps for shock absorbing traction. Yes, even the Vachetta linings, in all its shape accommodating and odor-controlling glory, are built into these boots.
Notably, the silhouette has an unnoticeable deviation from the standard Chelsea shape The almond-shaped toe box offers a lot of extra space, none of which can be seen from the outside. This gives your feet more breathability and comfort, while maintaining the sleek Chelsea look, thanks to the tapered waist.
And just like the Deans, the Boltons are equipped with a steel shank, fully riveted to the outsole and the insole, adding a reliable support and balance factor on top of that comfort.
What I Like
- With Beckett Simonon’s trademark shock-absorbing, extra bendy construction, these Chelseas are comfortable from the get-go, while providing more and more flexibility as you use them.
- Regardless of which of the four colorways you go for, the full-grain leather is attractive and will patinate exquisitely throughout time.
- These shoes are hand-made by craftsmen in Bogota, making each shoe like a piece of art.
What I Don’t Like
- There are some reports of this boot running large. Fortunately, the exchange process is pretty easy.
What Do Other Reviewers Say?
Reviewers are impressed with how slim and classy the boots look on the outside, but how much space there is on the inside.
As with the Deans and any made-to-order products, there is a significant wait time, but most agree that it’s fully worth it considering how much you save dollars-wise.
Again, there are a few almost-perfect reviews that mention the boots run large for them. One reviewer reports that they’re more like “military boot sizing.” However, these very same reviewers agree that the exchange process is always handled with excellent service.
The Verdict
The Bolton Chelsea Boots from Beckett Simonon are roomy and flexible, all thanks to the company’s signature hand-crafted construction. Despite the extra space inside, they’re designed with a chic taper that ensures the look isn’t compromised.
And of course, these boots are made with topnotch leather, making them fully worth the money, as long as you’re willing to wait for them to arrive.
Most Comfortable Black Dress Shoe: Suitsupply Tuxedo Oxford
Suitsupply makes more than just fast-tailored suits. They do some pretty good footwear, as well. Their Tuxedo Oxford Shoes are a great example, particularly because their super formal design might trick you into thinking they wouldn’t be as comfortable as they are.
These shoes have an Italian vibe about them, with the perfectly polished surface, incredibly satiny and sculptural architecture, and minimal but distinguished details. This is as dressy as it gets, though I’d argue you can still wear this in professional contexts (not just with tuxedos).
The calfskin upper and Blake stitching work together to give your foot a wide range of motion, without taking away from the liquidy smooth surface.
Moreover, the vamp is slightly lifted from the sides and the laces have a matte texturing, giving these shoes a modern and well-balanced look. They’re upscale, but not stuffy.
What I Like
- The flawlessly polished calfskin leather and clearly Italian-inspired silhouette give these shoes an undeniably lavish look, though the simple details keep them from being gaudy.
- With strong but finely-grained leather, and an immediately flexible sole, these shoes provide long-lasting comfort.
- Suitsupply implements carbon-neutral and waste-reducing practices.
What I Don’t Like
- I wouldn’t call this shoe high-maintenance, but you do need to polish patent leather footwear at least once a month so it stays strong, shiny, and protected against water. It’s certainly more maintenance than regular leather shoes, and if you’re me, it’s easy to forget to do it.
What Do Other Reviewers Say?
Reviewers agree that the shoes have a good-looking, Gucci-like shape about them that works perfectly with its high-shine leather.
Some reviewers disagree with me that these can be worn with suits and should be reserved for black-tie occasions. If you agree with them, you can add that to your own personal cons list, and that’s totally fine. Still, for around ~$300, these are worthwhile shoes given the comfort and quality even if you only wear tuxedos or tuxedo-equivalent black suits once a year.
The Verdict
With its fine-grained calfskin leather upper and easy-to-move-in outsoles, the Tuxedo Oxford Shoes from Suitsupply combine top-level formality with top-level comfort.
The highly polished and minimally detailed design checks most, if not all, the boxes when it comes to what we look for when we want black dress shoes.
The Suitsupply Tuxedo Oxfords are high-shine and immaculately designed dress shoes, perfect for the most formal of occasions. Surprisingly, they won’t restrict the movement of your feet, due to the flexible stitching and calfskin leather.
Most Comfortable for Standing and Walking: Wolf & Shepherd Monaco Loafer
Unsurprisingly, Wolf & Shepherd, the shoe company founded by a track and field athlete, has one of the most comfortable dress shoes for walking and standing.
There are two reasons why the Wolf & Shepherd Monaco Loafers are perfect for you on-the-go gents. First of all, they’re unlined, which means they’re much softer and far less stiff than their fully-lined counterparts.
Second, is the memory foam footbeds from FloatForm. Related to the first point, these footbeds are an excellent reason to keep the shoes unlined—a smaller barrier between you and this cozy material.
This is the same foam used for those high-end beds that contour to your body using your own body heat, which provides both a comfortable hug, and support to your bones. It also has a cooling effect. All of these benefits are activated the moment your feet sink into the shoes.
On the design front, the Monacos are penny loafers, with a posh European twist. Unlike authentic American penny loafers, there’s no beefroll, and the shape is slender but not pointy. That and the suede construction make these shoes appropriate in casual and formal dress codes.
Wolf & Shepherd is all about comfort and efficiency, as much as style. Their brand focus is evident in the fact they often use athletes like Rob Gronkowski and Steve Nash as spokespeople, over models and actors.
What I Like
- The interiors are completely unlined, providing a pliable and soft feel, whether you have socks on or not.
- With their memory foam footbeds, these shoes not only immediately and delicately conform to your feet, but provide structural support and a cooling effect.
- The flat American penny loafer style is infused with a European-esque taper, providing a look that’s both relaxed and formal.
What I Don’t Like
- The suede is beautiful, but can be difficult to maintain. The naps can pick up and trap dirt, so you may have to clean these shoes often depending on what you put them through.
What Do Other Reviewers Say?
Reviewers praise the Monacos for their soft suede uppers and their immediate comfort.
A lot of the reviewers are suit-and-tie professionals who do more than sit at a desk, which as mentioned, I am as well. I concur with them that these shoes are so comfortable that you can go from desk to meeting to hard-hat-adjacent spaces with ease.
The Verdict
If you need dress shoes that allow you to move around with ease, the Wolf & Shepherd Monacos, made by a brand fully focused on footwear that are comfortable for walking, are the perfect choice.
Their sleek take on the penny loafer design and suede construction makes them as adaptable visually, as they are functionally.
With their buttery suede uppers and slicker-than-usual penny loafer design, the Wolf & Shepherd Monacos can be worn practically anywhere. Even more, the memory foam footbeds and unlined interiors provide comfort, even when you’re standing and walking for long periods of time.
Most Comfortable Hybrid: Wolf & Shepherd Longwing
Here’s another entry from Wolf & Shepherd, and just like the Monacos, the Longwing Hybrids are made for walking–and then some.
As hybrids, the star of the show here is the thick, agile, and advanced sole system. The memory foam footbed is removable incase you prefer your own personal inserts.
The sole is high-density polyurethane, which means it’s both soft and highly elastic. Meanwhile the rubber outsole provides excellent grip, so you can head to the basketball courts right after work without changing shoes.
On top of that, literally, are handsome calfskin leather uppers that come in five colors.
What I Like
- With their fully athletic soles, the thermal rubber outsoles and the high-density TPUs work tougher to provide traction, energy-returning comfort, and minimal wear in the face of friction.
- Regardless of its sneaker-like support system, the uppers are still made of the same full-grain Italian leather you find on more traditional high-end dress shoes.
- The five colorways are classy, expressive, and yet neutral enough to partner with outfits of any color palette.
What I Don’t Like
- Though these shoes are a good option when it comes to hybrids, by nature, hybrids simply aren’t as versatile. You can’t wear these on formal occasions.
What Do Other Reviewers Say?
Reviewers love the fact that Wolf & Shepherd equips these shoes with actual full-grain Italian leather. Even though they’re hybrids, it’s a sign that they take the dress shoe side as seriously as the athletic side.
Many even report zero break-in time, which is worth mentioning since not all dress-sneaker shoes can make this claim.
The Verdict
Unlike so many hybrids out there, Wolf & Shepherd goes all in with both the dress shoe components and the sneaker components of the Longwings. The silhouette is like that of a more refined athletic shoe. The svelte upper brings a perfect balance to the thick energy-returning outsoles.
Most Comfortable Wingtips: Cole Haan Washington Grand Laser Wingtip
Not only are the Washington Grand Lasers from Cole Haan the most comfortable wingtips, but they’re also the upgrade pick.
The premium leather and slim silhouette are all there. Furthermore, and most importantly, these wingtips are filled to the brim with innovations, both functionally and aesthetically.
When it comes to style, the wingtip design is executed using a contemporary looking perforation, right on the uppers, versus on another piece of leather. This allows the shoes to keep its refined look while also adding unique character.
The EVA footbed and Cole Haan’s Grand.ØS technology not only provide cushioning, but arch support. And below that, you’ve got the leather outsoles meticulously engineered to mimic the natural motion of your feet, reducing the fatigue to almost zero.
What I Like
- The anatomic design of the footbed and Cole Haan’s in-house comfort technology provide heel-to-toe support that’s perfectly in-line with the natural movement of your feet.
- The unique look combines the refined simplicity of a slipper dress shoe with the details of a wingtip, offering a distinct and innovative look.
- The outsole boasts a debossed forepart providing flexibility, and a rubber heel cap for grip, partnering movement with security.
What I Don’t Like
- These shoes definitely run narrow, even for dress Oxfords.
What Do Other Reviewers Say?
Reviewers praise Cole Haan for designing such a contemporary shoe that can still blend in with classic wardrobes in both the professional and formal categories.
As I mentioned, there are some complaints about how narrow these shoes are. Even people with moderately wide feet who can comfortably squeeze into mediums, will have to go for wides.
The Verdict
Possibly the shoe of the future, Cole Haan’s Washington Grand Laser Wingtips flaunt a unique style that’s both modern and timeless, as well as impressive comfort technology. The systematic layers of proprietary materials provide support and fatigue-reducing softness, perfect for work, play, and just running errands.
Cole Haan combines traditional craft with contemporary technology in the form of the Washington Grand Laser Wingtips. The proprietary cushioning system on this sleek dress shoe provides comfort, arch support, and mimics the natural movement of your feet.
3 Ways to Make Your Dress Shoes More Comfortable
1. The Basics: Get the Right Size, Break Them In
This might go without saying, but you have to make sure you get the exact right size. While most brands conform to universal sizing, there’s always a little variation. If you’re typically a size 10, try a 9, a 9.5, a 10.5 and even an 11 to make sure you’re still a 10 with the particular brand you’re testing.
If you’re buying online, do your research and read reviews. The answers may very well be a few quick blurbs away.
Finally, most shoes need breaking in, so make sure you take the time to do that before putting your feet through an eight-hour work day in new footwear.
2. Maintenance: Conditioning, Resoling If Necessary
If you don’t keep your leather shoes clean and conditioned, they can get dry and tight or even loose and brittle. Neither situation would be comfortable or good for your shoes.
Meanwhile, if your outsoles are worn out, and you don’t resole them, not only will they make wearing your shoes an unpleasant experience, but it can also be really bad for your feet, ankles, and even calves.
3. Consider What You Wear Them With: Socks and Inserts
I know that it’s desirable to go for thicker dress socks in colder months, but if you go too thick, you’re basically sizing down the experience of the shoes as well. Go for socks that work smarter, not harder, like temperature-regulating fine wool socks, over heavily woven ones.
Ribbed socks provide mild compression to maintain blood flow. If you’re prone to swelling, then you might need proper compression socks.
And of course, you can’t go wrong with the right inserts.
Style, Meet Comfort
The Beckett Simonon Deans are our top pick because they’re true dress shoes with strategic construction that provides long-term comfort. This is also the case with the Bolton Chelseas.
The Beckett Simonon Deans are full-grain leather Oxfords that boast a high level of hands-on craftsmanship. At often ~$200, these classic, slim shoes fly miles over their price point. Oh, and they’re also super comfortable, to boot.
Looking for a full-grain leather dress shoe with athletic soles? Check out the Wolf & Shepherd Longwing. And from the very same brand, you can get the Monaco Loafers which are made for walking and standing.
With their buttery suede uppers and slicker-than-usual penny loafer design, the Wolf & Shepherd Monacos can be worn practically anywhere. Even more, the memory foam footbeds and unlined interiors provide comfort, even when you’re standing and walking for long periods of time.
Suitsupply even serves up a super formal black dress shoe that’s immediately comfortable.
Whether you work in a casual start-up environment where hybrid shoes are allowed, or a super formal buttoned-up office, one of these seven shoes can ensure you’re within code and perfectly comfortable.
FAQs
What brand of formal shoes are most comfortable for men?
When it comes to non-hybrid shoes, look for models that contour to your foot and regulate temperature. Two good brand examples include Beckett Simonon, who uses flexible Blake stitching, and Thursday Boots, who combines several comfort technologies with sturdy Goddyear-welted constructions.
Are Oxford dress shoes comfortable?
Well-built and broken in Oxford shoes tend to be one of the most comfortable dress shoes, which is why they’re such popular office shoes.
How do I make my dress shoes less uncomfortable?
Make sure they’re broken in before you wear them for long periods of time. Ensure you have the exact right size, and if you need them, find the right pair of inserts.
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