The Most Comfortable Dress Shoes for Men in 2024, Tested by Style Editors
<p>The most comfortable dress shoes we’ve tested have performance features like rubber, foam, and polymer soles. Their <a href=” target=”_blank”>insoles</a> 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.</p><h2 class=”body-h2″>What To Consider</h2><h3 class=”body-h3″><strong>Fit</strong></h3><p><strong></strong>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.</p><h3 class=”body-h3″><strong>Color</strong></h3><p><strong></strong>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.</p><h3 class=”body-h3″><strong>Sole Material</strong></h3><p><strong></strong>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.</p><h3 class=”body-h3″><strong>Upper Material</strong></h3><p><strong></strong>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.</p><h2 class=”body-h2″>How We Selected</h2><p>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.</p>”/>
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.
Sizes
6—13
Fit
Medium
Colors
Brown and black
Upper Material
Leather
Sole Material
Rubber
Advertisement – Continue Reading Below
Most Comfortable Wingtip Dress Shoe
Cole Haan ØriginalGrand Wingtip Oxford
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.
Sizes
7—16
Fit
Medium and Wide
Colors
Black/white, brown/white, brown/dark brown, black/black, gray/white, and oxblood/black
Upper Material
Leather
Sole Material
Rubber
Most Comfortable Slip On Dress Shoe
Florsheim Hamptons Moc Toe Venetian Loafer
Pros
Easy to slip on and take off
Can be worn with everyday fits
Cons
Not the most stylish option
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.
Sizes
7—14
Fit
Medium and Wide
Colors
Gray, black, cognac, brown, tan, navy, and blue
Upper Material
Leather or suede
Sole Material
Rubber
Most Comfortable Cap Toe Dress Shoe
Nunn Bush Centro Flex Cap Toe Oxford
Pros
Smooth toe cap design
Removeable insoles
Cons
One reviewer says shoe is a little too long and narrow
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.
Sizes
7—14
Fit
Medium and Wide
Colors
Black, brown, and cognac
Upper Material
Leather
Sole Material
Synthetic rubber
Advertisement – Continue Reading Below
Most Comfortable Dress Boots
Astorflex Bitflex Chelsea Boot
Pros
Classic Chelsea boot style
100% natural crepe rubber sole
Feels like walking on marshmallows
Cons
If you’re in between sizes, we recommend sizing down
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.
Sizes
7 – 14
Fit
Medium
Colors
Black, tobacco suede, stone suede, chestnut nubuck, and tan leather
Upper Material
Leather or suede
Sole Material
Crepe rubber
Advertisement – Continue Reading Below
Most Comfortable Luxury Dress Shoe
Crockett & Jones Hallam Cap-toe Shoe
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.
Sizes
6—14
Fit
Medium
Colors
Black
Upper Material
Leather
Sole Material
Leather with rubber outsole
Four More of the Most Comfortable Dress Shoes
Advertisement – Continue Reading Below
Nisolo Everyday Oxford
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.
Read more: Best Black Sneakers
Sizes
8—13
Fit
Medium
Colors
Black, brandy, brown, and tobacco
Upper Material
Leather
Sole Material
Leather with rubber outsole
Born Coquette
Born built an archetypical leather wingtip upper on a flat soled sneaker-style rubber sole. A padded insole provides an additional layer of comfort. The Croquette is truly the best of both worlds, making it an ideal office shoe.
Sizes
8—13
Fit
Medium
Colors
Blue, brown, and taupe
Upper Material
Leather
Sole Matterial
Rubber
Ecco ST1 Hybrid Plain Toe Tie
Ecco put a genuine athletic shoe sole on a luxuriously supple pebble grain leather. You could probably go for a long walk in the ST1 Hybrid if you needed to, although we don’t recommend it. However, kicking around in them for long days on the job or traveling is highly recommended.
Sizes
6—13
Fit
Medium
Colors
Brown, cognac, and black
Upper Material
Leather
Sole Material
Ecco Shock Thru composite sole
Advertisement – Continue Reading Below
How to Style Comfortable Dress Shoes
Comfortable dress shoes are an excellent suiting hack, as long as you stick to a pair that looks more traditional. For professional use, every workplace has different wardrobe guidelines, but wool, cotton, or blended slacks work pretty much universally. Chinos are a comfortable business-casual favorite that always look good with comfortable dress shoes, as long as your workplace allows them. As for above the waist, a collared dress shirt is never the wrong answer. Oxford shirts are pretty much the shirting equivalent of comfortable dress shoes: classic look with a cozy feel. Investing in some solid, dark colored crew neck sweaters in either wool or cashmere is a great office wear alternative for the colder months.
Christian Gollayan oversees e-commerce content for Men’s Health and Women’s Health. Previously, he was the Associate Managing Editor at TheManual.com. Christian’s work has also been featured in Food & Wine, InStyle, the New York Post, and Tatler Asia.