Top 15 Most Comfortable Dress Shoes for Men in 2017 [Complete Guide]

Top 15 Most Comfortable Dress Shoes for Men in 2017 [Reviews & Buying Guide]

Looking elegant and stylish is something that gives men a confidence boost, making us look better and potentially increasing our self-esteem. However, this won’t be as effective if the shoes are uncomfortable and make us feel bad when they hurt or damage our feet when they make it difficult to walk and even just because they don’t look good enough, so it is important that you learn how to choose.

That’s why we’ve decided to give you a glimpse of some of the most comfortable dress shoes for men, shoes that you will be able to wear in every situation where you need to dress up or just look more formal, that will both offer you good looking designs and the most comfortable overall you can think of.

Take a look further and find out more!

What to Look for When Finding the Most Comfortable Men’s Dress Shoes?

Mens Shoes Buying Guide

More than looking stylish and elegant, a dress shoe needs to be comfortable in order to give you enough confidence. When a shoe does not offer enough comfort, it will eventually make it harder for you to walk, to stand and to just use it, sometimes even decreasing your confidence and self-esteem.

On the other hand, you could be wasting a lot of money in a shoe that ends up being totally uncomfortable. You think it is comfortable when you used it for the first time, but later, it ends up being a total waste of money. For this, we’ve made a list of the factors you need to take into account when the most comfortable men’s dress shoes:


Something that it’s always important when choosing dress shoes is the support they offer in the heels, arch, and toes. You need to choose the ones that offer the best design in order to make it easier for you to walk and to just stand. Always look for those shoes who offer a good support on the feet, from the heel to the toes.


As said before, this part of the shoe is essential for comfort. However, it all depends on your type of feet. Some shoes won’t offer much comfort for people with high arches, while others won’t feel comfortable if they have flat ones. In this case, you need to look for those depending on your arches. But always make sure they are flexible in order to make it easier.


Some dress shoes tend to have a really big sole in the heel, plus an interior support that just doesn't offer much comfort. That’s why it is important to always find the shoes that better fit with you, as we always recommend those which are not too tall or too short, always looking for medium level for more comfort.


Maybe one of the most essential parts of looking for the most comfortable shoes, are the materials from which they are made. The materials of a shoe are of utter importance when it comes to comfort, depending on how well they are made and which materials are used, the comfort of the shoe will vary. You just need to look for those who are made of leather in the exterior and with comfortable rubber or silicon on the inside.

Top 15 Most Comfortable Dress Shoes for Men

There are thousands of dress shoes you could find on the market. However, what are the most comfortable dress shoes? Which are the ones that will offer more comfort and eventually be good-looking at the same time?

Here, we have a list of the 15 Most comfortable dress shoes for men reviews so you can learn more and choose according to your needs. Take a look:

The Walker Oxford shoes from Dansko are incredibly good for comfort and feeling good. What’s more, they offer a pretty good-looking design that will eventually offer a lot of advantages when it comes to walking and feeling comfortable. However, they only come in one color, even though they can still be worn in almost any situation, especially casual ones.

Dansko Walker Oxford


  • Very Comfortable for Casual Activities
  • Can be Worn on Almost any Situation
  • High-Quality Materials and Overall Design


  • Only One Color: Black
  • Toe Box can Feel A Little Small

If you’re looking for top-notch quality shoes that will offer superior comfort and the best overall experience with dress shoes, the Dansko Walker Oxford are exactly what you need. You won’t be disappointed in any way, as they’re made with superior materials and offer the best support that will satisfy you on almost every occasion you can think of. Even though they only come in Black color.

An affordable, classic, stylish, elegant and utterly comfortable. The ECCO Helsinski are a great pair of shoes that offer the best quality when it comes to comfort and materials at a price that can’t be beaten. What’s more, the support offered by this shoe is simply incredible, making it one of the most comfortable dress shoes for men standing and walking all day long.

ECCO Helsinki Oxford


  • Perfect for Standing and Walking
  • Superior Quality Materials
  • Perfect Support for More Comfort


  • Leather Can be Hard to Wash
  • Arch Support is Not Too Great

Even though this shoe offers a great price, the quality of its overall materials and design is top-notch above many of its competitors. It comes with imported leather, moisture-absorbing materials like linen and a great removable leather sole on the bottom of the shoe that also offers great support. These are simply the best shoes for walking and overall dressing options as they also look wonderful.

These shoes are not the best when it comes to looks, as they are simple but still pretty decent. However, what makes them good is their overall comfortability and wonderful materials that make them a long-lasting friend for almost any type of dressing, thanks to the overall design and wonderful thick sole.

Rockport Northfield Oxford


  • Thick And Supportive Sole
  • Wide and Comfortable
  • Lightweight and Flexible


  • Simple Design

These shoes are simply great when it comes to comfortability and good support. They have a thick sole that makes them supportive for almost any kind of activity, especially walking. Even so, they are still pretty light and really comfortable but don’t offer a great look, as they are simple and low-key style, mostly designed for people who work long hours. As a whole, they are just great and maybe the most comfortable dress shoes for men standing all day long.

Need to dress up and look seemingly elegant? The Dockers Gordon are perfect, as they offer a really comfortable feeling and experience plus the most functional good-looking design alongside a great overall quality. They are the most comfortable business casual shoes, one of the most preferred by business people.

Dockers Gordon Cap-Toe Oxford


  • High-Quality Materials
  • Easy to Clean and Make Shine
  • Good Looking and Awesomely Comfortable


  • Laces are Not the Best
  • Not For Everyday Use

The Dockers Gordon Cap are very good shoes that offer a great comfortability alongside the best high-quality leather. They are very liked by professionals in many fields, especially because they are cheap, good-looking and wonderfully comfortable, something that not many shoes offer. They are more than worth as dressing shoes.

Pretty comfortable leather shoes that offer a great brogue style for those who are looking for a more business-like look. However, they can still be used for almost any type of activity, as they help to look more as a dressing option but at the same time are comfortable and very high-quality that will last a long time.

Nunn Bush Nelson Wingtip Oxford


  • Great Cushion and Comfortability
  • Upper Comfortability
  • Wonderfully Looking


  • Very Expensive

As you see, these shoes are almost perfect. They offer the best comfortability, wonderful cushion, superior arch and heel support, and a great looking design. They are made with wonderful materials, especially the interior which comes on gel for better comfort. Overall, these shoes are wonderful and a very good option as they come in Cognac, Brown or Black.

The Hush Puppies Leverage are always well-made shoes thanks to the greatness of the brand. These shoes, in particular, are wonderfully looking, waterproof and help you maintain an overall good feeling throughout a long day of use on your feet, as they are also one of the most comfortable dress shoes for men.

Hush Puppies Leverage Slip-On


  • Great Leather Design
  • Great Toe, Arch, and Heel Support
  • Very Comfortable and Long-lasting


  • Shoe Gel Pad can Make it Uncomfortable

If you are looking for high-quality shoes in almost every way, these will be your best option for sure. They offer a great comfortability alongside a great design that will work for almost any kind of situation. What’s more, they are very affordable and offer great interior design, like the Shoe Gel Pad for more support, but that can eventually make it a little annoying. Overall, pretty good shoes for anyone who wants to dress.

Timberland is a shoe brand that creates well-made, good-looking and comfortable shoes for almost any type of use. But the Brook Park Oxford are simply one of the best without a doubt. These shoes are utterly comfortable, incredibly good-looking and offer wonderful support for any type of feet.

Timberland Brook Park Oxford Shoe


  • Wonderful Shock-Absorbing Feature
  • Perfect Arch Support for more Comfortability
  • High-Quality and Durable Materials


  • Can Get Difficult to Find the Right Size
  • Not Recommended for Outside Use

People who need comfortable and good-looking shoes that come at an affordable price while also giving the perfect sense of style, these shoes will make the perfect option. They also offer high-quality materials and are made with the best leather in the exterior which makes them just perfect. As a whole, these shoes are just great and one of the most recommended.

These well-built shoes are great for many things, even though they are not the best looking for their simple and not very interesting design. However, they offer a wonderful comfortability plus great high-quality and durable materials that make them waterproof and very useful for people who like to use these shoes for going out in different environments.

Dunham Burlington Waterproof Oxford


  • Wonderful Waterproof Feature
  • Comfortable, Casual and Good-Looking
  • Very High-Quality Materials


  • Can Feel A Little Stiff

As a whole, the Dunham Burlington Oxford Waterproof are affordable in their entirely and pretty worth for their price. If you want cheap shoes that will also last a long time while offering a high performance when it comes to comfort and use, you won’t find shoes as good as these. Perfect for casual use.

Even though Crocs have received a lot of bad and negative reviews due to their quality and overall looks, the Santa Cruz 2 Luxe Leather are really great and apart from whatever they’ve been offering before. These shoes are not only comfortable but really good-looking, something that’s not very common from Crocs.

Crocs Santa Cruz 2 Luxe Leather Loafer


  • Best of Crocs in Dressing Options
  • Wonderful Overall Support
  • Durable and Resistant Materials


  • Not as Good Looking as Other Options

They are wonderfully durable, high-quality and resist almost any type of environment. However, the best of them is their comfortability and good looks, as they are really good for all possible activities and still will help you maintain your feet feeling great. If you need quality shoes with a great comfortability and multiple uses, these shoes are perfect.

If you are looking for the most comfortable men’s dress shoes, the Bostonian Bolton Slip-On can be the answer you were waiting for. They work for both dressy and casual environments thanks to its greatly looking design in black leather that will make it just wonderful and fit any type of upper dressing.

Bostonian Bolton Dress Slip-On


  • Wonderfully Good-Looking
  • Overall High Comfortability
  • Black Leather Design is Top-Notch


  • Synthetic Sole May Not Last Long
  • A Little Expensive

If you want good-looking shoes for almost any type of use while also helping your feet feel great without any type of problem, these shoes are just perfect for you. They also come with different supporting features, like a great arch support, comfortable toe box, and a great heel height, even though the sole of this shoe is synthetic, making it a little less durable.

Clarks has always been a wonderful shoe-making company which is always at the top of the most comfortable dress shoes. And this is something they’ve maintained with the Clarks Colson Over Oxford, a type of shoe for almost anyone who’s looking for high-quality, stylish and simply wonderful shoes that will help you increase your overall comfortability.

Clarks Colson Over Oxford


  • Perfect High-Quality Materials
  • Good-Looking and Great Design
  • Offer the best Traction


  • Looks Are Not for Everyone

As dressing shoes, these ones are wonderfully supportive when it comes to traction, as they will help both to maintain a good and comfortable position while also helping you avoid slipping and such. What’s more, they are made with the best materials like polyutherane, goat suede, foam, and fabric, making them both wonderfully comfortable and long-lasting.

Carlyle from Allen Edmonds are wonderful shoes that offer an elegant, clean and stylish approach to dress while also being utterly comfortable for almost anyone and any type of use. They are perfect for people who love class but at the same time like a little outgoing and different environments, as they are made with the best durable and resisting material.

Allen Edmonds Carlyle Oxford


  • Classic and Elegant Style
  • Wonderful Overall Design
  • Very Comfortable and Durable


  • Not Recommended to Wash Them Too Often

These shoes are simply perfect for anyone who wants a classic style as a dressing option, offering the best comfortability due to its great materials like leather and a wonderful cushioning foam at the sole. They are simply reliable and good-looking, especially for people who like classic styles and a more stylish approach.

The Bruno Magli shoes are always one of the most comfortable dress shoes and the best when it comes to high-quality materials like goatskin, while also offering utter comfortability with great soft calf leather and possible, the best height materials ever, making them comfortable and shock absorbing without forgetting the ultra-good-looking style.

Bruno Magli Maioco Lace-Up Dress Shoe


  • Superior Style and High-Quality Looks
  • Comfortable and Supportive
  • Durable, Resistant and High-quality Materials


  • Very Expensive
  • Won’t Fit Casual Outfits

If you want gorgeous shoes plus a very comfortable feeling, these shoes will be perfect for you. What’s more, they will help you maintain your feet feeling wonderful, as the Bruno Magli Maioco are simply wonderful in almost every way possible, even though they are highly costly but always offering a higher level of dressing style.

When it comes to dressing shoes, Cole Haan is always one of the most used and known in the market. However, these shoes are almost perfect Wingtip shoes, both for their comfortability and overall looks. They come with great lace-up closures and an oxford style alongside a wonderful comfortability that makes them just great for any use.

Cole Haan LunarGrand Wingtip Derby Shoe


  • New LunarGrand Sole for Better Support
  • Good Looking and Stylish
  • Very Affordable


  • Materials Are Not Too Resistant

Offering a LunarGrand sole, a new type of sole specially designed for this shoe, you won’t find any type of discomfort, they will make your feet feel awesomely great and help you dress and look better with almost any type of outfit. And if this wasn’t enough, these shoes are also very affordable and one of the best of its kind.

Commonly named one of the most comfortable men’s dress shoes, the Johnston & Murphy Melton shoes are wonderfully comfortable and utterly good-looking. They also offer a perfect durable experience that makes them one of the best of their kind, especially for the perfect leather sole and overall design.

Johnston & Murphy Melton Oxford


  • Perfect Leather Sole for More Comfortability
  • Good Looking and Elegant
  • Comfortable and Versatile Shoes


  • Heel Height is a Little Too Tall

If you want well-constructed shoes while also having comfortability and a very good looking design at the same time, you won’t find a better option than the Melton Oxford. These shoes will help you create a wonderful comfortability and enough support for your feet, whole also being totally affordable and simply fitting almost any type of situation.

Need Comfortable Shoes to Dress?

As you see, the most comfortable dress shoes for men are simply wonderful when it comes to both looking great and eventually helping yourself have a better walking and standing experience at the same time. However, their best feature is being able to help you dress in different situations from casual to formal, and they won’t do any harm.

But as you see, you will need to choose correctly if you want to eventually get the right option, depending on your needs and desires. That’s why you can find more than enough information about the previously reviewed shoes, as we want to help you choose the ones that better fit with you.

Take a look at our most comfortable dress shoes for men reviews and make sure you pick the ones that help you have better comfortability and make you look better at the same time. Take our recommendations into account and you will see how great they are! Remember to take into account their price & reviews, you won’t like to eventually choose incorrectly!

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