There are many reasons why you may find yourself wearing dress shoes regularly. For the working man, a workplace dress code may require them. For others, sporting a dapper pair of formal shoes may simply be a matter of personal preference.
And while they’re known for being stylish, dress shoes are hardly known for being comfortable. In fact, they have a reputation for being the exact opposite: stiff, cumbersome, and unforgiving on your feet.
If you’re hesitant to wear formal footwear because of the expected discomfort, there is hope yet. Advances in shoe technology have ushered in a new era of modern dress shoes that combine remarkable comfort with timeless style cues.
After personally trying dozens of pairs, we’ve selected the most comfortable ones and featured them on this page. Yet, if the styles we feature here don’t quite fit your needs or style preferences, we’ve also covered the characteristics you need to consider when shopping for a new pair on your own.
The following guide will help you know exactly what to look for and what to discard when searching for the ideal pair of cozy dress shoes.
What Is The Most Comfortable Brand Of Dress Shoes?
When it comes to the most comfortable brand of dress shoes, it should come as no surprise that comfort is not about any particular brand. Indeed, comfort is subjective, and what matters most is finding the brand or brands that suit your specific needs.
Additionally, consider the role you expect the shoe to fill i.e., the occasion in which you’ll be using them. For example, traditional dress shoes can still offer comfort when worn for special events like weddings, but they may not be the ideal choice for the demands of a 9 to 5 office job.
Below, we cover both classic dress shoes that provide the most comfort, as well as styles more suited for heavy wear. Browse them and consider how they’d fit your lifestyle, as in the end, it’s all about finding the right balance of style and comfort that works for you.
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- Style: Oxford Shoe
- Formality: Business Professional
- Pricing: $175.20* [Buy From Beckett Simonon]
* With “BU20” Discount Code
If you’re not particularly fond of high-tech materials and modern concepts, we highly recommend Beckett Simonon for a classic dress shoe aesthetic. Benchmade in Colombia, these shoes are manufactured from Gold Standard full-grain Italian leather with a traditional Blake stitch construction.
Admittedly, we struggled to choose a favorite model from Beckett Simonon’s catalog. However, the Dean is a timeless cap-toe Oxford that will be incredibly versatile whatever your needs. And with our 20% discount code “BU20“, they come in comfortably under the critical $200 price point.
Although Goodyear welting is often seen as the pinnacle of craftsmanship, there is much to be said for the Blake stitch. Notably, Blake stitch breaks in much faster than Goodyear welt, so it’s more comfortable to wear right out of the box.
Additionally, this construction is more flexible and often lighter than a bulky Goodyear-welted shoe, making for agile wear. Finally, the inside is lined entirely with leather, and the leather insoles will mold to your foot over time, ultimately providing a custom fit.
- Style: Longwing (Hybrid)
- Formality: Business Casual
- Pricing: $289 [Buy From Wolf & Shepherd]
Wolf & Shepherd is a premium brand that produces some of the world’s most comfortable dress shoes for men. If you’re like us, you may be somewhat skeptical of all the hype. However, we have tried a number of their shoes ourselves and can now attest to how the proprietary sole technology may earn you all-day comfort!
By melding calfskin leather uppers with high-density TPU soles, they’ve managed to bring a modern element to classic styles. Additionally, as they’re quite light, you won’t experience fatigue even when wearing them for extended periods. All things considered, they’re one of the most comfortable men’s dress shoes we’ve ever come across.
Lastly, if the brand name sounds familiar, it’s because their Crossover lines of shoes, including these Longwings, have garnered quite a bit of traction online and in the mainstream.
- Style: Derby
- Formality: Business Casual
- Pricing: $189 [Buy On Amberjack]
While Amberjack’s The Original isn’t a dress shoe in the traditional sense, times are changing and business casual is becoming more common in settings that formerly commanded strict dress codes.
Amberjack’s founder, John Peters, sought to create a versatile shoe brand that produces affordable yet comfortable footwear. To achieve this, he teamed up with designer John Kraljevich who has worked with brands including Allen Edmonds, Coach, and John Varvatos. You can learn more about its full story with our review.
The resulting flagship model, The Original, is a hybrid that marries traditional craftsmanship with modern athletic footwear technology. Its footbed is three times thicker than those from similar brands and features heat-activated arch support. Meanwhile, the lightweight outsole provides both stability and traction while the supple American cowhide uppers offer excellent comfort. Most recently, the brand has also introduced Chelsea boot styles employing the same comfort-imparting technology.
The comfort, styling, and value for money have earned The Original a well-deserved spot on our list.
"Amberjack's The Original offers a comfortable and casual option for the professional man on the move."
- Style: Brogues
- Formality: Business Professional
- Pricing: From $265 [Buy From Ace Marks]
If you’re looking for a more outgoing style, Ace Mark’s Italian-made Vincent was one of our top picks when considering unique style and comfort. Thanks to a Blake Flex construction, these dress shoes offer added flexibility and heightened comfort.
Similarly, they’re crafted from supple calfskin leather uppers, which molds to the wearer’s feet over time. Combining impeccable style with traditional Italian craftsmanship, these are certainly worth your attention.
If you’re not fond of the burgundy and tan full-grain leather upper combination, there are plenty of other colorways available through their site linked above.
- Style: Brogues
- Formality: Business Casual
- Pricing: $395 [Buy Now On Zappos]
Interestingly, the Allen Edmonds Strandmok is one of the first pairs of men’s dress shoes that we reviewed on Bespoke Unit. After all this time, it still remains one of our favourite pairs and easily outperforms many newcomers.
Although crafted with the Allen Edmonds 360° Goodyear welt, they’re flexible and offer a pleasant stride. This is partly thanks to the striking Dainite rubber sole that provide excellent shock absorption.
The Allen Edmonds Strandmok is available in a variety of styles with some more formal than others. However, we’re great fans of the distressed brown, which is made from a supple calfskin leather upper. As a wingtip Oxford brogue shoe, it’s less formal than a cap toe Oxford. Nevertheless, it should be fine in some offices.
- Style: Made To Order
- Formality: Varies
- Pricing: From $335 [Buy Now On Idrese]
Manufactured in Almansa, Spain, Idrese produces Goodyear-welted men’s dress shoes at very competitive prices. Most notably, they’re completely customizable and made to order, which means that you can design them yourself using its website’s interactive tool! Many styles are available, from wingtip Oxford dress shoes to a cap-toe monk strap. The choice is yours!
We’re impressed by both the quality and value Idrese provides. However, we were particularly surprised by the comfort of its shoes, too. Indeed, Paul Anthony, Bespoke Unit’s founder, often struggles to find shoes that fit.
Fortunately, Idrese has a vast selection of sizes and widths. Paul was able to order his shoes in 14EEE, and he was amazed by the comfort that they provided. Finally, you can also choose between leather and rubber soles depending on the shock absorption you want.
- Style: Kiltie Loafer
- Formality: Business Casual
- Pricing: $190 [Buy Now On Lethato]
Not only does Lethato’s kiltie slip-on loafers feature an unusual and original design, but they’re also made in India! Indeed, Lethato is a proudly Indian up-and-coming dress shoe brand that offers hand-painted footwear at excitingly tempting prices.
Its price points vary depending on whether you opt for Goodyear-welted and Blake-stitched shoes. In the case of the kiltie slip ons, they feature a Blake stitch. The unique design combines a monk strap, a kiltie vamp, and wingtip broguing. It may not be to everyone’s taste, but it certainly stands out!
A cushioned footbed offers comfortable support and rubber outsole provide additional grip. Admittedly, the loafers aren’t incredibly comfortable out of the box. Indeed, they have a tendency to briefly pinch as the last has a different shape. However, within just a day, they will have broken in to provide as much comfort as any of the other dress shoes listed here.
- Style: Service Boot
- Formality: Business Professional
- Pricing: $207* [Buy On Beckett Simonon]
* With “BU20” Discount Code
Chukka boots are often very casual in appearance compared to a typical dress shoe. Yet, Beckett Simonon has successfully redefined the style to offer a more premium and elegant aesthetic. The result is the Lopez, which is a low ankle-length boot made with a Gold Standard Italian calfskin leather upper.
Inspired by the boot’s First World War heritage, it offers style and function. Like the Dean Oxford shoes, the Lopez features a Vachetta leather lining, which is smooth and comfortable. Furthermore, the rubber sole provides comfortable shock absorption.
- Style: Penny Loafer
- Formality: Business Professional
- Pricing: $374.95 [Buy Now On Zappos]
Although we appreciate Mephisto’s quality, we tend to avoid its men’s dress shoes as they’re not particularly attractive. However, the Cap Vert is certainly an exception. As a spenny loafer, they’re a business casual option. Therefore, we wouldn’t pair them with a suit but they’re an excellent choice when being up on your feet all the time.
As slip-on loafers, they’re very convenient. Furthermore, extra padding in the tongue reduces pressure points.
Meanwhile, an extra soft leather lining is designed with a special Air-Relax cushioned insole for additional breathability. Therefore, they’re an excellent option in any season.
- Style: Derby Shoe
- Formality: Business Professional
- Pricing: $200 [Buy Now On Zappos]
Ecco is a celebrated comfortable dress shoe brand. Often marketed as a cheaper alternative to Mephisto, its men’s dress shoes can occasionally be a little too utilitarian for dressy wear. As a result, people often just opt for Cole Haan instead. However, the Ecco Citytray is a wonderful exception.
Opting for a classic Derby design, it’s not quite as formal as some of the Oxford shoes featured elsewhere in this list. However, it’s understated and good enough for both office and catering work.
The insole is removable so you can use your own. Furthermore, it features lightweight Fluidform Comfort Technology soles. As the name suggests, it also uses Ecco’s Tray technology that provides additional stability and grip, which is perfect when on the move.
How Can I Make My Dress Shoes More Comfortable?
If you’ve already purchased a pair of dress shoes and found them uncomfortable, there are some options to alleviate your discomfort.
Shoe Stretchers
If your shoes feel too tight, consider using shoe stretchers, which are available for purchase on Amazon. These devices are designed to gently stretch the shoes, relieving pressure points that may cause discomfort.
However, it’s important to use them cautiously, as pushing the shoes’ materials to the limit can result in damage that leaves you with no shoes at all.
Break Them In
New dress shoes often need time to loosen up and mold to your feet, which can improve comfort. That being said, there’s a balance to strike here.
While it’s true that new shoes may become more comfortable with wear, excessively uncomfortable shoes are unlikely to transform into your most comfortable pair. Be mindful not to fall into the trap of hoping they’ll get better over time, especially if you’re buying them because you really like how they look.
Consider Custom Insoles
If you’ve tried different dress shoe brands and still haven’t found the right pair, custom insoles may be the way to go. That’s because these tailored inserts offer personalized support and cushioning, ensuring your shoes fit your feet perfectly.
To get custom insoles, visit a podiatrist or a specialized shoe store for fitting. While there might be an initial cost, the long-term comfort and foot health benefits are worth every penny. Additionally, custom insoles can often be used in different pairs of shoes.
Keep in mind that you should have the insoles on hand when purchasing a new pair of dress shoes. Check that both insoles & shoes fit together well, and most importantly, that they in fact provide pain-free wear when used in combination.
Choose Wisely
Our selection of comfortable dress shoes above showcases various styles and brands, many of which offer different widths to ensure a good fit.
Given the array of options available, it’s not worth taking a chance on shoes that aren’t comfortable from the start. Investing time to find the right fit initially can save you from purchasing uncomfortable dress shoes you may never wear.
Additionally, leverage the return policies that most shoe sellers offer. Buy a couple of pairs, try them on at home (don’t wear them excessively), and return the pairs that aren’t comfortable right out of the box.
How To Find Most Comfortable Dress Shoes For Men
When people mention dress shoes for men, the first image that comes to mind is sluggish footwear that’s stiff and causes blisters. However, we’ve come a long way from the wood and leather apparatus from centuries ago.
Since most of us still wear harmful footwear, we’re at risk of ailments such as Plantar Fasciitis or overpronation. Yet, thanks to the advances in men’s dress shoes, you can now wear formal dress shoes that are just as comfortable as slip-ons or running shoes!
In the next section, we cover some of the features that you should look for to ensure you find the most comfortable pair of dress shoes for you.
Key Features for Ultimate Comfort
Achieving the utmost comfort in your dress shoes requires attention to detail. Here are some essential considerations:
1. Correct Fit: Begin by determining your accurate shoe size. Many people underestimate their actual size, so measure your feet and consult a sizing guide for a precise fit.
We’ve put together a guide on how a shoe should fit, so check it out to see if you run into any problems with your usual footwear.
2. Foot Shape: Different dress shoe brands may have unique last shapes, impacting how well they conform to your feet.
For instance, even common brands like Cole Haan and Johnston & Murphy have surprisingly different shapes! Familiarize yourself with your foot’s shape and explore brands that match it.
3. Arch Support: Understanding your arch height is crucial. Proper arch support ensures comfort and prevents issues like bruising or overpronation. Refer to our arch support guide for more insights.
4. Breathable Materials: Opt for shoes with leather linings or breathable synthetics. These materials allow air circulation, reducing sweat and the risk of blisters.
5. Cushioning: Look for dress shoes with cushioning, a feature borrowed from athletic footwear. Cushioned insoles provide comfort by reducing pressure on your feet’s contours.
6. Stability: While cushioning is essential, it should not compromise stability. Ensure a balanced shoe design to maintain proper gait and prevent ankle discomfort.
7. Ankle Grip: Shoes with ankle notches or collars secure your feet in place, minimizing friction and preventing blisters.
As you may have noticed, many of these features can only be determined by having the shoes in front of you. At this point, we’ll once more stress that you should leverage return policies before settling on a final pair of shoes.
All in all, by taking these features into consideration when shopping for dress shoes, you can elevate your comfort and enjoy a pain-free experience throughout the day.
What Next?
Now that you have read about the most comfortable men’s dress shoes, you can read some of our other related guides to dress shoes and other types of shoes:
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Hi, How To Wear- This topic is really helpful and 100 unique
Thank you for the comment, and we’re glad you found it helpful.
Cheers – Paul
this is a very helpful and unique post. I have learned a lot of things from this post. And all these shoes are really nice and look so much fashionable. Have to buy one for me pretty soon.
Thank you for this post. Informative and helpful.