If you’re always wearing a suit or adhering to a dress code for long periods of time, you will need comfortable dress shoes or it’s simply unbearable.

Therefore, this guide will present you with the top 10 best most comfortable dress shoes for men:

  1. Oxford Shoe: Beckett Simonon Dean
  2. Wingtip Shoe: Ace Marks Vincent
  3. Business Casual: Amberjack The Original
  4. Oxford Shoe: Wolf & Shepherd Longwing
  5. Brogue Shoe: Allen Edmonds Strandmok
  6. Custom Shoe: Idrese
  7. Kiltie Loafer: Lethato
  8. Boot: Beckett Simonon Lopez
  9. Loafer: Mephisto Cap Vert
  10. Derby Shoe: Ecco Citytray
  11. Brogue Shoe: Rockport Tanner

Interested in a particular pair? Just click on the link above to jump right to it! Otherwise, scroll down to see them all. At the end of this guide, we’ll also detail what to look for in dress shoes for comfort.

What Are The Most Comfortable Men’s Dress Shoes?

Advert Title Text Banner Zappos Mobile Link Block Ad

See All Bespoke Unit Dress Shoe Guides

Read Now

1. Beckett Simonon Dean [Oxford Shoe]

Becket Simonon Dean Oxford on paisley carpet

* With “BU20” Discount Code

Shop Now

If you’re not particularly fond of high-tech materials and modern concepts, we highly recommend Beckett Simonon as a worthwhile alternative. Benchmade in Colombia, these men’s dress shoes manufactured from Gold Standard full-grain Italian leather with a traditional Blake stitch construction.

Admittedly, we struggled to choose a favourite model. However, like the Wolf & Shepherd Closer above, the “Dean” is another timeless cap toe Oxford that will be incredibly versatile whatever your needs. And with our 20% discount code “BU20“, a pair costs the same as Cole Haan dress shoes!

Although Goodyear welting is often seen as the pinnacle of craftsmanship, there is much to be said for the Blake stitch. Firstly, a Blake stitch breaks in much faster than Goodyear welt, so it’s more comfortable to wear right out of the box.

Additionally, it’s more flexible and often lighter to wear than a bulky Goodyear-welted shoe. Beckett Simonon also uses chromium-free vegetable-tanned wholecut linings in their shoes. Therefore, you don’t experience any chafing on the stitch work. Therefore, they’re an impeccable choice when on a budget.

2. Ace Marks Vincent [Brogue Shoe]

Ace Marks Vincent Brogues
Shop Now

If you’re looking for a more outgoing style, Ace Mark’s Italian-made Vincent was our favourite model from the brand that provided the most comfort. Thanks to a Blake Flex construction, these men’s dress shoes offer added flexibility, which heightens the comfort.

Similarly, they’re crafted from supple calfskin leather uppers, which moulds 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 colourways available through their site linked above.

3. Amberjack The Original [Derby Shoe]

Amberjack The Original Shoe Sole Detail
Shop Now

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.

Conclusively, 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."
Bespoke Unit Rating: ★★★★★

4. Wolf & Shepherd Longwing [Hybrid Shoe]

Wolf & Shepherd Crossover Longwing In Maple White Calfskin
Shop Now

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 memory foam 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 of time. Ultimately, at this price point, they’re one of the most comfortable men’s dress shoes we’ve 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 as well as in the mainstream.

5. Allen Edmonds Strandmok [Brogue Shoe]

Allen Edmonds Strandmok Brogues
Shop Now

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.

6. Idrese [Custom Shoes]

Idrese Shoe Review
Shop Now

Manufactured in Almansa, Spain, Idrese produces Goodyear-welted men’s dress shoes for less than $300. Furthermore, they’re custom shoes, 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, Bespokes 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 them. Finally, you can also choose between leather and rubber soles depending on the shock absorption you want.

7. Lethato [Kiltie Loafer]

Lethato Kiltie Shoes
Shop Now

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.

8. Beckett Simonon Lopez [Formal Boot]

Beckett Simonon Lopez Boots

* With “BU20” Discount Code

Shop Now

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.

9. Mephisto Cap Vert [Loafer]

Mephisto Cap Vert Penny Loafer
Shop Now

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.

10. Ecco Citytray [Derby Shoe]

Ecco Citytray Plain Toe
Shop Now

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.

11. Rockport Tanner [Brogue Shoe]

Rockport Business 2 Wingtip Brogue
Shop Now

If you’re on a strict budget, Rockport is a reliable dress shoe brand that you can trust. While Cole Haan or Johnston & Murphy dress shoes are typically chosen on this budget instead, Rockport has many benefits for comfort. The Tanner range offers some decent-looking wingtip Oxford shoes that you can easily wear for different occasions.

For instance, it features a removable OrthoLite footbed, which is a great brand of comfortable inserts. Meanwhile, its lightweight rubber outsole will help absorb shocks and provide you with extra grip.

Although not the best men’s dress shoes on this list, these wingtip Oxford dress shoes have earned their place thanks to both their price point and reliably.

How Can Dress Shoes Be Comfortable?

Wolf & Shepherd Closer Cap Toe Sole & Upper

When people mention the 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 dress shoes, you can now wear formal footwear a particular dress code that’s just as comfortable as slip ons or running shoes!

In this section, we’ll explore the features to look for in the best men’s dress shoes that ensure all-day comfort.

Best Comfortable Dress Shoe Features

Shoe horn in brown dress shoe

Firstly, we can’t stress how important it is to make sure that your dress shoes fit correctly. You can start by adequately learning the size of your feet as most people don’t know their real size.

Read up on how a shoe should fit to see if you run into any problems with your usual footwear.

Similarly, you should become familiar with the shape of your feet. After experimenting, you may notice that not every dress shoe will fit your feet perfectly due to differences in last shapes.

For instance, even common brands like Cole Haan and Johnston & Murphy have surprisingly different shapes!

Furthermore, people may have different arch heights in their feet. It’s essential to be aware of you arches as this can drastically affect the comfort of your dress shoe. You can learn more about this with our dedicated arch support guide.

Finally, the features that you should look for in comfortable shoes are the following:

  • Breathable Materials: Leather lining and some synthetics let your feet breathe, which reduces perspiration and prevents blistering.
  • Arch Support: As mentioned above, you’ll need to have the right arch support to accommodate for yours and ensure all-day comfort. Too much can cause bruising while too little results in overpronation.
  • Cushioning: A trait of athletic footwear that’s being seen more and more in dress shoes, cushioning secures the feet and reduces pressure on its contours.
  • Stability: Too much cushion can reduce security and affect your gait. Therefore, a careful balance will ensure you walk correctly and avoid any ankle discomfort.
  • Ankle Grip: Features such as ankle notches or collars will ensure that the foot sits securely in the shoe. This reduces rubbing and prevents the development of blisters.

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:

Shoe Content

Shoe-Homepage Shoe-Style-Guides Shoe-Color-Coordination Shoe-Care-Button Shoe-Reviews