Whether you’re standing all day or suffer from conditions such as plantar fasciitis, comfortable dress shoes are a necessity for the office or formal occasions. Not only do you require an ergonomic balance of support and cushion but it’s crucial that the shoes are presentable.

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

  1. Oxford Shoes: Wolf & Shepherd Closer
  2. Oxford Shoes: Beckett Simonon Dean
  3. Wingtip Shoe: Ace Marks Vincent
  4. Brogue Shoes: Allen Edmonds Strandmok
  5. Dress Boots: Wolf & Shepherd Breakaway
  6. Custom Shoes: Idrese
  7. Brogue Shoes: Rockport Business 2
  8. Formal Boot: Beckett Simonon Lopez
  9. Chukka Boot: Ugg Dagmann
  10. Business Casual: Mephisto Cap Vert

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 so that they’re comfortable.

Wolf & Shepherd Breakaway Boots On Box

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What Are The Most Comfortable Dress Shoes For Men?

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1. Wolf & Shepherd Closer [Comfortable Oxford Shoe]

Wolf & Shepherd Closer Cap Toe Oxford Shoe
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Wolf & Shepherd is a premium shoe brand that produces some of the world’s most comfortable dress shoes. If you’re like us, you may be somewhat sceptical of all the hype. However, we have tried a number of their shoes ourselves and can attest to their all-day comfort!

By adhering to classic styles and traditional calfskin leather uppers, their shoes look like any other business shoe. However, they cleverly conceal features such as EVA heels, memory foam cushioning,  lightweight leather soles, and engineering support.

As a result, they’re the most comfortable dress shoes that we’ve worn so far. As they’re quite light, you won’t experience fatigue even when wearing them all day long.

"Elegant and sophisticated Oxford shoes, nobody will release the unparalleled comfort that they other until they try them on."
Bespoke Unit Rating: ★★★★★

2. Beckett Simonon Dean [Oxford Shoe]

Becket Simonon Dean Oxford on paisley carpet

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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, they’re manufactured from Argentinian full-grain calfskin with a traditional Blake stitch construction.

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 use 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.

3. Ace Marks Vincent [Wingtip Shoe]

Ace Marks Vincent Brogues
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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, they offer added flexibility, which heightens the comfort.

Similarly, they’re crafted from supple calfskin leather, 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 leather combination, there are plenty of other colourways available through their site linked above.

4. Allen Edmonds Strandmok [Brogue]

Allen Edmonds Strandmok Brogues
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Interestingly, the Allen Edmonds Strandmok is one of the first pairs of 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 a 360° Goodyear welt, they’re flexible and offer a pleasant stride. This is partly thanks to the striking Dainite rubber soles that provide excellent shock absorption.

The 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.

5. Wolf & Shepherd Breakaway [Dress Boot]

Wolf & Shepherd Breakaway Boots Feature
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Another excellent creation by Wolf & Shepherd, the Breakaway boot was a later introduction following the brand’s critically-acclaimed success. Indeed, it’s an excellent addition to their growing line-up.

Not only do you enjoy all their usual features and precision engineering, but you also benefit from the added ankle support too. As a result, the Breakaway boot is a wonderfully comfortable boot that is perfect for intensive use.

Although they a great business casual option, the use of a cap toe means that they can also be worn formally. We’ll often wear them with jeans and then polish them up to go with a three-piece tweed suit.

6. Idrese Custom Shoes

Idrese Shoe Review
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Manufactured in Almansa, Spain, Idrese produces Goodyear-welted shoes for less than $300. Furthermore, they’re custom shoes, which means that you can design them yourself using its website’s interactive tool!

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.

7. Rockport DresSports Business 2 [Brogue]

Rockport Business 2 Wingtip Brogue
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Rockport’s new aptly named “DresSports Business 2” range offers an affordable selection of professional footwear. If you’re tempted by Wolf & Shepherd’s footwear but don’t have the necessary budget, they’re a great alternative.

Their truTech technology offers excellent shock absorption while the cushioned insole provides the necessary comfort required for all-day wear. We’re particularly fond of the brogue in cognac or dark brown. However, there’s a rich variety of styles that may be more suitable for you everyday needs.

8. Beckett Simonon Lopez [Formal Boot]

Beckett Simonon Lopez Boots

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Although chukka boots are often very casual in appearance, Beckett Simonon have successful redefined the style to offer a more premium and elegant aesthetic. The result is the Lopez, which is a low ankle-length boot made from Argentinian full-grain calfskin leather.

Inspired by the boot’s First World War heritage, it offers style and function. Like the Dean Oxford shoes, the Lopez features a vachette lining, which is smooth and comfortable. Furthermore, the rubber soles provide comfortable shock absorption.

10. Ugg Dagmann [Chukka Boot]

Ugg Dagmann Chukka Boot
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Most of us probably associate Ugg with big comfy angle-high slippers for women. However, the brand has largely surpassed this popular yet polarising footwear. Today, it offers a wide selection of shoes and boots for both men and women.

We were taken aback by Ugg’s stylish chukka boots. Not only do they look fantastic but they perform well as comfortable dress shoes. The boots are designs with the brand’s own enerG Comfort System. Consequently, it provides built-in arch support in the form of an additional layer of open-cell PU foam.

If you’re looking for a formal boot, the black pair are probably your best bet. Yet, we’re quite fond of the brown’s suede effect.

How Can Dress Shoes Be Comfortable?

Wearing Semi-Formal Attire At ONE Dine RestaurantWhen people mention dress shoes, 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 running shoes!

In this section, we’ll explore the features to look for in formal footwear that can ensure all-day comfort.

Comfortable Dress Shoes Features

Shoe horn in brown dress shoe

Firstly, we can’t stress how important it is to make sure that your 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 all shoes fit your feet perfectly due to differences in lasts.

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 shoes. 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 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:

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