Most Comfortable Dress Shoes For Men: Top-rated Formal Footwear For Style & Comfort

Most Comfortable Dress Shoes For Men: Top-rated Formal Footwear For Style & Comfort2018-10-11T08:36:46+00:00

You soon realise that comfortable dress shoes are of vital importance if you’re standing all day or spend most of your time in formal environments. At Bespoke Unit, we often wear dress shoes so we’re more than aware of this!

In this guide, you will discover and be able to pick up the most comfortable dress shoes for men:

  1. Oxford Shoes: Wolf & Shepherd Closer
  2. Classic Oxfords: Beckett Simonon Dean
  3. Wingtip Shoes: Wolf & Shepherd Senna
  4. Dress Boots: Wolverine 1000 Mile Cordovan
  5. Brogues: Allen Edmonds Strandmok
  6. Penny Loafers: Mephisto Cap Vert
  7. Venetian Loafers: Ecco Illinois Slip-On
  8. Orthotic Friendly: Rockport Almartan

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.

Becket Simonon Dean Oxford Pose

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Quick Buyer’s Guide

In a rush and want to jump straight to the shoes? Just use our Quick Buy Guide below to pick up a pair! However, you can learn their individual details by scrolling down.

Oxford Shoes

Wolf & Shepherd Closer Cap Toe Oxford Shoe

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Oxford Shoes

Becket Simonon Dean Oxford Dress Shoes

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Wingtips

Senna Wingtip Brown Comfortable Dress Shoes

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Dress Boots

Wolverine Original 1000 Mile Cordovan Boot

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Brogue Shoes

Allen Edmonds Strandmok Brogues

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Penny Loafer

mephisto cap vert penny loafers

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Venetian Loafer

Ecco Illinois Slip On Shoe

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Orthotic Shoes

Rockport Almartin Brogue Shoe

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See All Bespoke Unit Dress Shoe Guides

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What Are The Most Comfortable Dress Shoes For Men?

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1. Wolf & Shepherd Closer Cap Toe [Oxford Shoes]

Wolf & Shepherd Closer Cap Toe Oxford Shoe
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Overview

Wolf & Shepherd are a premium footwear brand whose claim to fame was creating a classic dress shoe that is exceedingly comfortable. With a construction inspired by athletic footwear, these shoes offer features such as EVA footbeds and supportive midsoles.

How To Wear

Whatever formal needs you may have, the Closer Cap Toe is a shoe style that can accommodate a whole range of dress codes. WHether your needs are the office, formal gatherings or lavish cocktail soirées, these will blend right in.

Best Colors

For more casual dress, there’s also the option to opt for “maple” mid-brown or “honey” tan leathers. However, if you’re looking for a formal dress shoe, black is always a solid choice.

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2. Beckett Simonon Dean [Classic Oxford Shoes]

Becket Simonon Dean Oxford Dress Shoes
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Overview

Whilst these are classic Oxfords like the pair above, they’re not only more affordable but are made using more traditional methods. Handmade from Argentinian calfskin, they offer excellent quality given the price point.

How To Wear

Ideal for business and professional wear, these sleek Oxfords can also be worn for more formal occasions too. These are an excellent choice for everyday professional wear.

Best Colors

If you’re looking for a more casual shoe, then brown is a very good option. However, black leather is always the best choice when seeking to cater to formal requirements.

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3. Wolf & Shepherd Senna [Wingtip Shoe]

Senna Wingtip Brown Comfortable Dress Shoes
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Overview

An alternative to Wolf & Shepherd’s Close Cap Toe is the Senna Wingtip. If you’re looking for a flashier shoe style that offers the details of a brogue without becoming too informal, these are a beautiful specimen.

How To Wear

Known as blind brogues, these feature the same details as a brogue save for the medallion on the toe cap. This makes them a more streamlined style, which is slightly more formal than full brogues.

Best Colors

Like the Oxfords, these brogues are available in a maple mid-brown or honey tan. However, if you want to go for a more formal style, they’d also look great in black, which is rare for brogues.

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4. Wolverine 1000 Mile Boot [Versatile Dress Boots]

Wolverine Original 1000 Mile Cordovan Boot
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Overview

If you’re more fond of boots and want a comfortable and dressy option, Wolverine have a versatile offering. With optimal ankle support as well as a comfortable footbed, these are great for all-day wear. After all, they’re good for 1000 miles!

How To Wear

As Paul highlights in his review linked below, he emphasises just how versatile these boots are to wear. Whilst they’re great for casual wear, you could even wear them with a suit for a more business professional look.

Best Colors

For versatile wear, we’re very fond of the Cordovan No.8 leather. However, if you needs are more formal, there’s a beautifully eye-catching black option too.

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5. Allen Edmonds Strandmok [Brogue Shoes]

Allen Edmonds Strandmok Brogues
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Overview

With the Dianite soles that offer comfort return when walking, Allen Edmonds have created and beautifully stylish and elegant brogue. Similarly, a cushioned insole makes these very comfortable indeed.

How To Wear

Although more casual as the options above, we still find these to be fantastic dress shoes. If you’re fond of tweeds, then they’re perfect for this sort of formal wear. Meanwhile, they’re fantastic as business casual footwear as they look wonderful with chinos and a sport jacket.

Best Colors

Unfortunately, these are only available in brown so you can’t wear them more formally. However, the shade of brown offered is stunning. It has an aged vintage look, which looks great when worn. There’s also a touch of tan in the welt as well as rust red Dianite soles.

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6. Mephisto Cap Vert [Penny Loafers]

mephisto cap vert penny loafers
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Overview

Although not strictly a dress shoe, the penny loafer is a very comfortable footwear style for less formal attire. With its EVA footbed and subtle orthotic design, Mephisto have made a very cosy shoe.

How To Wear

As mentioned above, these aren’t particularly formal shoes and at the very limit of dressiness. Therefore, it’ll be hard to wear these with a suit unless it’s the summertime. On this occasion, it’s a great option to pair with a beige suit.

Best Colors

Whilst we quite like the laid-back attitude of the tan loafers, they’re also available in a Cordovan shade, which is equally if not more elegant. However, we’d refrain from the black leather as it’s slightly too dressy for the shoe style.

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7. Ecco Illinois Slip-On [Venetian Loafers]

Ecco Illinois Slip On Shoe
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Overview

With the ECCO Comfort fibre system and a removable leather covered inlay sole, these loafers are very comfortable to wear. If you’re looking for an understated and subtle dress shoe, they’re an excellent solution.

How To Wear

These are best reserved for professional wear where you’re on your feet all day yet requires a relatively formal shoe. However, they’re not necessarily the best choice for formal occasions where you want to look stylish.

Best Colors

If you want something a little more casual, you can opt for the walnut brown, which is somewhat more stylish. However, if you’re looking for a more formal look for work or other occasions, black is the way to go.

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8. Rockport Almartin Brogues [Orthotic Dress Shoes]

Rockport Almartin Brogue Shoe
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Overview

Like Vionic, Rockport is well-known for making orthotic shoes that don’t look too clinical. Their approach is quite similar and these shoes also feature an EVA footbed that offers both stability and cushioning for a comfortable and corrected gait.

How To Wear

We think these are great for business professional wear with a classic-cut suit. However, you could probably push it all the way up to cocktail attire as they’re really rather stylish for orthotic shoes!

Best Colors

Currently, these brogues are only available in black, which is ideal for more formal wear. If you’re looking for brown brogues, we’d recommend the Allen Edmonds Strandmok above.

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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 properly. You can start by properly learning the size of your feet as most people actually 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 important 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 you 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 whilst 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 stability 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:

Most Comfortable Men's Dress Shoe Guide
Reviewed by Jeremy C., on .
"Comfortable without cutting on style. I still look great without killing my feet!"
Rating: 5.0 ★★★★★

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