The Most Comfortable Dress Shoes for Men in 2024, Tested by Style Editors

Cole Haan's Wingtip Oxford and the Florsheim Hamptons are two of our top picks.

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The Most Comfortable Dress Shoes for Men in 2024, Tested by Style Editors

MEN'S DRESS SHOES have remained relatively unchanged for the past century. We’re still wearing oxfords and derby shoes with plain toes, cap toes, and wingtips. Loafers still come in the penny, tassel, and venetian varieties. The biggest change in dress shoes is how we wear them. Nowadays, guys want dress shoes that are as comfortable as they are handsome, and our favorite menswear brands have happily obliged, churning out top-notch tuxedo shoes, slip-on shoes, and even dress slippers with next-level cushioning found in some of our favorite walking shoes.

Today, the most comfortable dress shoes have soles that cushion and cradle our feet, absorb the pressure of our steps, and provide superior traction. Dress shoe uppers have also been upgraded with padding around the ankle, in the tongue, and interiors. Most importantly, all these changes have been made without changing the overall appearance of dress shoes that we know and love.

The most comfortable dress shoes we've tested have performance features like rubber, foam, and polymer soles. Their insoles contain memory foam and gel pads at key pressure points, especially the heel, which makes them look and function more like orthopedic inserts than old school leather and cork insoles. Many comfortable dress shoes even replaced heels with flat, sneaker-like soles. For long days at the office, long nights on your feet, or just striking that balance between looking classy and feeling comfy, these are the most comfortable dress shoes for men right now.

Just as with any other shoe, finding the right fit is nailing that middle ground between cramped and loose. If your feet are compressed for long periods of time it can not only cause foot pain but negatively affect the rest of your body by throwing off how you naturally carry your weight. Too much room, on the other hand, and you will cause friction that results in blisters. When you try on a pair of shoes, make sure you can wiggle your toes and spread them out. Comfortable dress shoes avoid the pointed toes that looked nice on some traditional dress shoes, but are not friendly to toes. You also want to make sure your heel sits firmly against the back of the shoe as you take a few steps.

To maintain a proper dress shoe look, you want to stick with the usual colors like black, brown, gray, blue, and cognac for the upper. If you’re going with suede, a lighter sandy tan color is a good choice. Soles may contain composites of various materials but they should be a uniform color, or close to. A solid black, brown, or white sole is preferable. Contrasting between the sole and upper is a good look, like a brown upper and white sole for instance. Avoid bright colors or sporty patterns that you might find on a sneaker.

All three layers of the sole have seen significant upgrades in comfortable dress shoes. Insoles are more comforting with modern materials like memory foam and gel pads. Midsoles are ergonomically shaped to provide arch support, heel cradling, and absorb toe pressure. Whole slippery leather outsoles have been replaced with firm gripping rubber. Whether you go for a classic heel or an athletic style flat sole, your feet are getting pampered.

There are plenty of comfortable dress shoes out there that have strayed too far into athletic shoe territory by ditching the leather, or at least leather-looking uppers. It is important not to lose the “dress” part of dress shoes by wearing something that looks like a fancy trainer. The best shoe makers are using softer, more accommodating leather to retain that familiar dress shoe look while enhancing comfort. The rule of thumb is: As long as the upper looks dressy, the sole can be more athletic.

Our team of Men's Health style editors and writers have collaborated extensively to identify the most comfortable dress shoes for men. Over the past few years, we've researched and tested more than four dozen shoe models from various top-rated brands including Amberjack, Cole Haan, Florsheim and more.

Ecco does an excellent job of concealing all the comfortable upgrades to keep the Citrytray Cap Toe looking like an old school dress shoe. The removable orthopedic insole, which is replaceable when it wears out, is even covered with a layer of leather to look like an old fashioned dress shoe on the inside. Ecco's Citrytray midsole and outsole system provides the kind of traction and stability you find in a walking shoe. A simple cap toe derby in brown or black is as useful and reliable a dress shoe as you can find. This will keep your feet happy at work, on wedding dance floors, and any time you're on the move.

Step into something comfortable first before you step into success, like in these business casual shoes that are nothing but supportive and stylish. Having owned and worn these for several months, I can say with confidence that these are perhaps the most comfortable dress shoes I’ve ever tested—all thanks to Amberjack’s athletic performance build. The memory foam arch support plus the flexible outsole with extra support in the heel are both designed to let your feet move in comfort, and the upper is made with flexible materials. The construction makes it a pair of dress shoes that won’t tire my feet out since it's soft and easy to break in yet very sturdy.

Some comfortable dress shoes take clear inspiration from sneakers, the DresSports from Rockport is one of them. While this is essentially a plain toe leather derby, the rubber midsole and ankle padding come from more casual footwear. Those tweaks are made without disrupting the overall dress shoe look. The all white sole contrasts nicely with the brown or black upper to create a business causal look. These are great work shoes laidback office dress codes.

Read more: Best Men's Leather Sneakers

Wingtip dress shoes are one of those old-fashioned styles that have managed to stick around because they just always work. Whether you're rocking a t-shirt and jeans or a three-piece suit, wingtip oxfords place the perfect accent on your fit. Up top, Cole Haan nails the classic look with just enough brogue detail (those perforated holes in the leather) to show off the wing design without overdoing it. While several layers of cushion and support in the insole and midsole pamper your feet. You can go with black or white leather in either black or white soles, plus there is a gorgeous oxblood leather option with a black sole.

Venetian loafers have a sleeker aesthetic than penny or tassel loafers because those extra details are removed. Florsheim makes an elevated slip on comfortable dress shoe with their venetian style Hamptons. The molded rubber sole has a slightly athletic look but the matte black color keeps it dressy. These are great for weddings, social events, and just dressing up for the fun of it on your time off.

These may look like some standard issue cap toe oxford shoes, but Nunn Bush packed the insole and midsole with soothing little details. Gel and foam inserts support your weight and provide bounce in your step. Flexible midsoles and outsoles bend in a natural motion with your feet as you walk. The heel is low to prevent too much pressure on the balls of your feet. These are classic formalwear shoes to wear with suiting or office attire.

Nubuck leather is buttery soft and much easier on your feet than a standard leather dress shoe. Johnston & Murphy added a mesh lining on the inside to help your feet breath and cut down on weight. The result in a chocolate brown upper that looks great and feels even better. On the inside, you've got a removable memory foam insole over a bouncy composite foam outsole. These beauties will keep the pep in your step during long days at the office. Plus, they look great with chinos and slacks.

G.H. Bass makes some of the worlds finest loafers at very friendly prices. The signature Weejuns penny loafers typically come in all leather but a far more comfortable alternative is the suede upper with EVA sole. Suede and softer and more flexible so there is little-to-no breaking in required. You also get that fuzzy matte texture which looks great with jeans and chinos. Most of the comfort, however, comes from the EVA sole which is lighter, more flexible, and provides a bouncy step, compared to leather soles. It is also much cheaper to resole.

Chelsea boots are not only the dressiest of all boot varieties, they are also one of the most popular footwear options for men this fall. Astorflex makes one of the most comfortable Chelsea boots out there and they look fantastic, to boot. The leather is soft and flexible, requiring minimal breaking in. The gusset is extra wide providing ample flexibility in the ankle. Best of all is the cushioning and traction provided by the crepe rubber sole. It acts like a natural spring, expanding and contracting with every step, while gripping to the ground as you walk. Dress them up with slacks or chinos, or go rugged with jeans.

A sandy suede wingtip derby is the perfect fall dress shoe. It works well with slacks and chinos at the office and plays well with jeans on the weekends. Allen Edmonds built the Williams Wingtip Derby with signature XL Extralight injection molded outsoles to cut down on weight and provide cushioning in your step.

Crockett & Jones is one of the most well respected shoe makers in the world. The brand shows that using the absolute best materials and craftsmanship can provide as much comfort as the best performance sneakers out there. Every piece of this shoe is hand crafted to provide your feet with maximum comfort. If your budget allows for there, there is no better experience for your feet.

Black oxford shoes look good with just about everything. Nisolo set the Eevryday Oxford apart with a custom designed five layer memory foam insole that keeps your feet happy all day. The wider, boot style toe box also provides ample room for your toes to spread naturally as you walk.