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:
- Oxford Shoes: Wolf & Shepherd Closer
- Classic Oxfords: Beckett Simonon Dean
- Wingtip Shoes: Wolf & Shepherd Senna
- Dress Boots: Wolf & Shepherd Breakaway
- Brogues: Allen Edmonds Strandmok
- Penny Loafers: Mephisto Cap Vert
- Venetian Loafers: Ecco Illinois Slip-On
- 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.
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
Oxford Shoes
Wingtips
Dress Boots
Brogue Shoes
Penny Loafer
Venetian Loafer
Orthotic Shoes
See All Bespoke Unit Dress Shoe Guides
Other Boot Guides
- Comfortable Work Shoes [Coming Soon]
- Comfortable Shoes For Men
Recommended Shoe Guides
- Style: Oxford Shoes
- Formality: Business Professional
- Pricing: $345 [Buy From Wolf & Shepherd]
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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- Style: Oxford Shoe
- Formality: Business Professional
- Pricing: $199 [Buy From Beckett Simonon]
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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- Style: Blind Brogues
- Formality: Business Professional
- Pricing: $365 [Buy From Wolf & Shepherd]
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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- Style: Blucher Boot
- Formality: Business Casual
- Pricing: $395 [Buy On Wolf & Shepherd]
Overview
As comfortable boots go, the Breakaway boots by Wolf & Shepherd are hard to beat. Between the memory foam footbed, EVA heel and lightweight construction, they’re well-made for ensuring all-day comfort no matter the punishment that they take.
How To Wear
Furthermore, they’re very versatile. These boots can be worn both formally on business or even as casual footwear. Overall, whether you’re wearing suits or jeans, they look great.
Best Colors
For a more formal boot, consider the black Onyx calfskin. Meanwhile the cognic while be a versatile choice and the honey tan would be the most casual.
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- Style: Brogues
- Formality: Varies
- Pricing: $345 [Buy From Allen Edmonds]
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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- Style: Penny Loafers
- Formality: Business Casual
- Pricing: $350 [Buy Now On Amazon]
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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- Style: Venetian Loafer
- Formality: Business Professional
- Pricing: $260 [Buy Now On Zappos]
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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- Style: Brogues
- Formality: Business Professional
- Pricing: $119.95 [Buy Now On Zappos]
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?
When 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
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:
- Top 10 Best Men’s Dress Shoes
- Best Dress Shoes Under $500
- Best Shoes For Flat Feet
- Best Shoes For Standing All Day
- Bespoke Unit Shoe Homepage
"Comfortable without cutting on style. I still look great without killing my feet!"Rating: 5.0 ★★★★★
Shoe Content
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