The 14 Most Comfortable Dress Shoes for Men in 2023

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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.