The 14 Most Comfortable Dress Shoes for Men in 2023

Based on customer reviews and editor testing

ONE37pm editors select every item that appears on this page, and the company may earn compensation through affiliate links within the story. You can learn more about that process here.
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Dr. Martens, Marc Nolan, G.H. Bass

The holiday season and start of the new year is finally here. Perhaps you have multiple holiday and work events you're attending these next couple of months. Maybe you plan to go on vacation and there’s several parties and events taking place that you’ll need to be dressed in your Sunday best for. Whatever the occasion might be, it’s likely that you will need a nice pair of dress shoes for all of your upcoming events. Such as the case with many formal shoes, you don’t just want a shoe that’s easy on the eye, you also want something that’s comfortable and goes along nicely with your suits, dress shirts, and blazers. Long gone are the days where we suffered in the name of looking good. With so many brands having made technical updates made to shoes, it’s more than possible to find a dress shoe that both looks and feels good. To help you out, we’ve put together a list of the most comfortable dress shoes for men, but before we get started there’s a few things you need to know first.

RELATED: The 26 Best Waterproof Sneakers to Keep You Covered This Spring

Things to Consider When Picking a Comfortable Dress Shoe:

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Calvin Klein

Finding the Right Footbed: How should a dress shoe fit? First of all, you have to take into consideration that no one foot is like the other. Just because something worked for your father or your brothers, doesn’t automatically mean it will work for you. To measure your footbed, you will need to have both of your feet traced. From there, draw a straight line through the middle and mark where your heel and longest toe ends. The distance between them is the length of your midsole. Now that you know your measurements, you’ll be able to pick an insole that goes directly with your foot size. 

Leather or Non-Leather Sole: You’ll also need to find out what material your desired shoe is made out of. The biggest difference between leather and non-leather soles is that leather soles break in and mold to accommodate your feet over time.

However, that doesn’t automatically mean that you won’t find comfort with other materials. Rubber, for example, is flexible right off the bat and built to have more shock absorption so that you don’t feel the pavement as much when walking. Ultimately the decision to go with leather or non-leather depends on your personal comfort level and how long/much you want to wear the shoes you purchase. Rubber doesn’t age well, so if you plan on wearing your shoes a lot (or want to keep them for a long time), then leather might be the way to go.

Fit: We kind of touched on this a bit earlier, but the overall fit of the shoe is a very important factor to consider when shopping. Width is particularly important in men’s shoes, as not all shoes are built to accommodate wider feet. The difference between whether or not your toes are hitting the top of the shoe pretty much depends on the width. Of course this can be hard to assess online as you are unable to try the shoes on in person to see how they feel, but if you know your foot measurements, then that can put you in a better position to have more success with the fit.

The Most Comfortable Dress Shoe for Men, At a Glance:

1. Magnanni Palos Oxford Men

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The Sleekest Oxford

  • Sizes: 40-46
  • Widths: M
  • Colors: Curri
  • Upper material: Leather
  • Sole material: Rubber
  • Shoe type: Oxford
  • A promising review: "I bought these shoes (and matching belt) for an event that I went to. The rubber soles are nice, and the shoes are very comfortable- not too narrow in the toe." - Nordstrom Reviewer

Magnanni offers a classic shoe that has long been highly reviewed and a favorite amongst men when it comes to dress shoes. Dressed in a sleek smooth Curri color with a vintage-but-still modern oxford style, the shoes feature a burnished finish to add to that modern feel, while also offering a cushioned insole with arch support to help you remain comfortable all day. Additionally, these shoes are waterproof, which always an added bonus.


2. Clark's Suede Desert Boot

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Most Comfortable Dress Boot

  • Sizes: 7 to 14
  • Widths: M
  • Colors: Black, Cola, Beeswax, Brown, Sand, Dark Green, Greystone, Brown/Orange, Light Green
  • Upper material: Suede
  • Sole material: Crepe
  • Shoe type: Dress Boot
  • A promising review: "This is a classic shoe that breaks in over time and becomes super comfortable and form fit to your foot. I wore them a lot when I was younger, and still have a pair today." - Charlie Kolbrener, Managing Editor at ONE37pm

Continuing upon the influential design first created in the 1950s, the Clarks Desert Boys have been popularized and worn by beatniks, mods, Britpop bands, and Jamaican rude boys everywhere from Europe to Jamaica. While everything is attractive about the shoe, its standout features are most definitely the crafted, clean lines and unique lace fastening. In addition to the standard black color, there's also eight other colors to choose from including brown and light green, so you have plenty of options at your disposal.


3. Cole Haan Men’s OriginalGrand Energy Twin Oxford

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Cole Haan

Most Affordable Dress Shoe

  • Sizes: 7 to 13
  • Widths: M
  • Colors: Black, British Tan
  • Upper material: Leather
  • Sole material: Rubber
  • Shoe type: Oxford
  • A promising review: "Any customer would say how comfortable and great Style the Cole Haan held in their shoes... I complete my outfit with a pair of Cole Haan every time I dress up." - Cole Haan Reviewer

We've said this before and we'll say it again—few do it better than Cole Haan in the dress shoe department as their shoes are stylish, durable, and affordable. Being one of the best men's footwear lines in the game, they obviously have a ton to choose from, but our favorite is their Original Energy Twin Oxford as it comes in two versatile colors (black and british tan), has moisture-wicking textile, and rebound technology, and a GRANDFØAM footbed for extra cushioning.


4. Cole Haan Men's Modern Classics Penny Loafer

Cole Haan

Most Comfortable Penny Loafer

  • Sizes: 7.5 to 13
  • Widths: M
  • Colors: Noire, British Tan, Black Patent
  • Upper material: Patent leather
  • Sole material: Leather
  • Shoe type: Loafer
  • A promising review: "I like simple dress shoes that can be used with lots of my suits. I am also always thinking about comfort and these shoes I wear on the road and at all day conferences. They look great, travel great, and feel great." - Michael Kolbrener, father of Charlie Kolbrener, Senior Editor at ONE37pm

The Berm Plain Toe Derby is a shoe that has been in high demand since its release. The best place at having a chance to grab a pair for yourself is at Nordstrom in terms of color and sizing option. Why is this shoe in such demand you ask? In addition to its affordability, the Derby's are also crafted with a minimalist style that has become popular in the world of men's fashion lately. While this probably won't be a shoe to last you for years, it will definitely get the job done for the next couple of summers.


5. Allen Edmonds Park Avenue Dress Shoe

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Allen Edmonds

Most Comfortable All-Black Shoe

  • Sizes: 6.5 to 14
  • Widths: B, D, E, EEE
  • Colors: Black, Chili, Bourbon Brown
  • Upper material: Calfskin Leather
  • Sole material: Customizable
  • Shoe type: Oxford
  • A promising review: "A comfortable shoe I can wear in any setting." - Allen Edmonds Customer

Allen Edmonds has a range of comfortable dress shoes for men including their Park Avenue Oxford Dress Shoe which was first introduced as a part of their core lineup in 1982. The Park Avenue Oxford boasts loads of cool features including a relaxed fit that can be dressed both up and down, comfortable insoles that provide enhanced support, flexible rubber cup soles, and more.


6. Dr. Martens Adrian Smooth Leather

Dr. Martens

Most Comfortable Business Casual Shoe

  • Sizes: 6 to 14
  • Widths: M
  • Colors: Black
  • Upper material: Leather
  • Sole material: Leather
  • Shoe type: Loafers
  • A promising review: "I bought these a bit too small intentionally to allow them to break in to the shape of my foot. It paid off wonderfully; they're now one of my most comfortable and easiest to wear pair of shoes." - Charlie Kolbrener, Managing Editor at ONE37pm

A 1970s inspired shoe with a smooth design, the Adrian Smooth Leather Tassel loafers are a slightly modernized take on a classic. Honing in on its subculture influence, the shiny leather and tassel's are what make these shoes standout, along with the fact that they can be worn with pretty much everything. While these shoes are recommended for normal to wide feet, they will need to be broken in as they are pure leather which is something to keep in mind.


7. Wolf & Shepherd Swiftknit Derby

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Most Comfortable Casual Shoe

  • Sizes: 6 to 15
  • Widths: M
  • Colors: Black, Navy, Black/White, White, Denim, Pine
  • Upper material: Leather-lining
  • Sole material: Rubber
  • Shoe type: Derby
  • A promising review: "Best shoes I have ever bought. Bought a second pair soon after I bought the first" - Scott, Nordstrom Reviewer

Sometimes you want the best of both worlds—a dressy shoe with the comfort of a sneaker. So how about combining the two and getting a dressy sneaker. Wolf & Shepherd has a cool pair of derby's that features a timeless classy design of a dress shoe in the form of sneaker. Speaking of comfort, the derby's are built with a flexible knit construction featuring a sheepskin lining and smart arch support. If you want to learn more about Wolf & Shepherd, check our interview with them here.

SHOP NOW AT NORDSTROM, $98.45 – $179.00

8. G.H. Men’s Larson Weejuns Loafer

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G.H. Bass

Another Comfortable Penny Loafer

  • Sizes: 7 to 13
  • Widths: M
  • Colors: Black, Whiskey, Wine
  • Upper material: Leather
  • Sole material: Leather
  • Shoe type: Loafer
  • A promising review: "Love the shoe! Probably the best shoe I’ve ever put my foot on. Better than it looks online. Just what I was searching. My shoe for the 20’s!" - G.H. Bass Customer

G.H. Bass is another place to grab an excellent pair of dress shoes. Their Weejun's Penny Loafer is designed to have the genuine comfort of a moc shoe, while still being dressy and elegant enough to be able to wear to formal events. Crafted in El Salvador in a beefroll-style, these shoes are available in either a black, whisky, or wine color, and have received quite a few positive reviews about the comfort.


9. Amberjack Loafer

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Most Comfortable Leather Shoe

  • Sizes: 7 to 13
  • Widths: M
  • Colors: Chesnut, Honey, Obsidian, Grizzly, Cobalt, Tundra, Slate
  • Upper material: Full-grain Leather
  • Sole material: Leather
  • Shoe type: Loafer
  • A promising review: "I have had great difficulty in recent years in finding loafers which fit well at a reasonable price; many seem to lack a firm hold at the heel even when the size is otherwise correct. This shoe, however, fits well and holds my foot well at the heel. It was comfortable out of the box - no breaking in needed. I shall certainly look into - and look forward to - different shoes from Amberjack." - Malcolm, Amberjack Buyer

Perhaps the coolest thing about the Amberjack Loafer is heat-activated arch support. That's right, the shoes are built with a specific foam that uses heat to form to your foot. Heat is always good for relaxing the muscles, so no doubt you'll be comfortable while wearing these. Additionally, the Amberjack Loafer's are made with A-Grade leather, along with a high-performance dual-density outsole for extra flexibility and protection.


10. Marc Nolan Jasper Black Leather Wingtip Sneakers 2.0

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Marc Nolan

Most Comfortable Dress Sneaker

  • Sizes: 6, 7, 8
  • Widths: D
  • Colors: Burgundy, Cognac
  • Upper material: Full-grain Leather
  • Sole material: Shock-absorbing EVA Sole
  • Shoe type: Wingtip Sneakers
  • A promising review: "These shows are awesome. My husband wore them with a suit. He says they are comfortable & he loves the look." - Amy, Marc Nolan Reviewer

The Marc Nolan Jasper Wingtip Sneakers are a shoe that is regularly in heavy demand and hard to get your hands on. Described as a wear-with-anything shoe, the sneakers can be dressed up to wear suits, or dressed down for casual wear depending on the occasion. Versatility is something that is very important if you are going to make an investment in dress shoes, and the Jasper Wingtip Sneakers meet the qualifications.


11. Amberjack Original Dress Shoe

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Best Dress Shoes for Standing

  • Sizes: 7-13
  • Widths: M
  • Colors: Honey, Chesnut, Onyx, Obsidian, Honey & Cream, Chesnut & Cream, Stone, Slate, Grizzly, Carbon, Cobalt
  • Upper material: Leather
  • Sole material: Leather
  • Shoe type: Oxford
  • A promising review: "Most comfortable and stylish shoe I have worn in a while. I was hesitant to order at first because its a new company but seriously the quality of the shoes is on par if not better than high end shoe companies. Also as a side note they have amazing customer service!" - Nick, Amberjack Buyer

Same deal as the loafers. The oxford version aka "The Originals" have the same type of heat-activated arch support, along with being crafted in A-Grade leather. The Originals also have the same dual-density outsoles as the loafers, and strong hiking boot material in the back that allow you to wear them all day with causing discomfort to your feet.


12. Paul Stuart Charles Leather Lace Up

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Paul Stuart

Best Luxury Dress Shoe

  • Sizes: 7-13
  • Widths: N/A
  • Colors: Black
  • Upper material: Leather
  • Sole material: Rubber
  • Shoe type: Classic Lace-up
  • A promising review: "I personally tested the Charles Leather Lace Up by giving this to a male relatively in my family. The shoes fit him nicely, working well with the bulk of his work outfits, and accommodated his perfectly as far as comfort with him having a wide foot. Months later, the shoes still look like we got them yesterday making it a great choice for those considering. - Jael Rucker, ONE37pm Style and Entertainment Editor

With an overall design and structure that works for all foot types, Paul Stuart's Charles Leather Lace-Up is cut with an all-leather upper, a Damian rubber sole, and features a classic five eyelet design. Uber comfortable and especially good for those with large wide feet, this style is simple, sleek, and easy to pair with lots of different outfits. Due to the construction the wear and tear is limited, and the shoes age nicely looking just as new one year in as what they did the day you purchased.


13. Ponto The Pacific

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Ponto Footwear

Best Shoe for Walking

  • Sizes: 8.5-14
  • Widths: M
  • Colors: Oak, Black, Slate Blue, Lagoon, Obsidian, Nimbus Grey, Desert Orange, Citrine, Camel
  • Upper material: Leather
  • Sole material: Sugarcane foam
  • Shoe type: Part dress shoe, part sneaker
  • A promising review: "They’re quite comfortable, very lightweight and I appreciate their simple design." - Scott, Ponto Footwear Buyer

If you are looking for a shoe to walk in comfortably all day, Ponto had you covered with their "Pacific" shoe, which is a part dress shoe, part sneaker. Made with eco-friendly bio-based materials, these shoes come with many other quality features worth the buy such as being water repellent, odor-resistant, and durable. With a variety of colors available, you should have no problem finding one that best suits you.


14. Berluti Lorenzo Drive Leather Loafer

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Most Comfortable Luxury Shoe

  • Sizes: 6 to 12.5
  • Widths: M
  • Colors: Visone
  • Upper material: Camoscio Leather
  • Sole material: Leather
  • Shoe type: Part Loafer
  • A promising review: "Berluti has long been in the business of delivering comfortable shoes that are also the definition of opulent and luxury. These are no different." - Jael Rucker, ONE37pm

If luxury is what you are looking for specifically, Berluti's reputation for making beautiful dress shoes emphasizing comfort is unparalleled. In fact, the newly added addition to their Maison loafer collection, The Lorenzo Drive, is already receiving rave reviews due to their sleek, elongated shape, and fine details. The Lorenzo is a great shoe whether you are taking meetings at the office, or going on a date night.  


Why trust ONE37pm:

Each of these selections were carefully handpicked by member of the ONE37pm staff. While we certainly wanted to select shoes that were visually appealing, the main focus was on the comfort as that remains the most important factor in our book for footwear. Knowing now that ill-fitted footwear not only causes comfort in the immediate, but also in terms of long-term foot health, it's especially important to pick shoes that are made with comfortable material.

For this article, I spoke with our Managing Editor and shoe expert Charlie Kolbrener to hear a bit about how he identifies a comfortable pair of shoes for the day. Charlie has spent years wearing and testing numerous dress shoes, and was able to provide some insight into the best options that remain comfortable over long periods of time.

How we conducted our research:

According to a 2021 footwear study conducted by Hylton B. Menz and Daniel R. Bonanno entitled Journal of Foot and Ankle Research, comfort can be defined as "the state of being physically relaxed and free from pain, although the mere absence of pain does not fully constitute the positive state of being comfortable." Additionally, the use of comfortable footwear is also considered to have a range of practical advantages, as it may "facilitate physical activity and reduce the incidence of injury."

While a lot of the data from this study is a bit fragmented, they did find that "well-fitted, lightweight shoes with soft midsoles and curved rocker-soles are generally perceived to be most comfortable." We took this info into consideration when making our selections.

RELATED: The 13 Most Comfortable Nike Shoes for Standing All Day in 2023

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