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.
Most Comfortable Dress Shoes
- Best Overall Comfortable Dress ShoeEcco Citytray Cap ToeRead more
- Most Comfortable Business Casual Dress ShoesAmberjack The OriginalRead more
- Most Affordable Comfortable Dress ShoeRockport DresSports 2 Go Plain Toe ShoeRead more
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.
What To Consider
Fit
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.
Color
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.
Sole Material
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.
Upper Material
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.
How We Selected
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.
Best Overall Comfortable Dress Shoe
Ecco Citytray Cap Toe
Now 25% Off
Pros
- Made with rich leather, which will last a long time
- Sole reduces bulk for added flexibility
- Durable stitching throughout the silhouette
- Has a removable leather-covered insole for more comfort
Cons
- Comes in two colors
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 |
Most Comfortable Business Casual Dress Shoes
Amberjack The Original
Pros
- Water-repellent Italian suede and sheepskin lining
- Covered by 2-year warranty
- Sizes range up to 15
Cons
- May have to size down if you’re in between sizes
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.
| Sizes | 7—15 |
|---|---|
| Fit | Standard |
| Colors | 12 options to choose from |
| Upper Material | Leather or suede |
| Sole Material | Thermoplastic polyurethane |
Most Affordable Comfortable Dress Shoe
Rockport DresSports 2 Go Plain Toe Shoe
Now 25% Off
Pros
- Offers lightweight shock absorption
- Breathable fit
- EVA heelcup makes shoe comfortable enough for all-day wear
Cons
- Only one color option available
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
| Sizes | 7—15 |
|---|---|
| Fit | Medium |
| Colors | Caramel and black |
| Upper Material | Leather |
| Sole Material | Rubber |
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Most Comfortable Wingtip Dress Shoe
Cole Haan ØriginalGrand Wingtip Oxford
Now 24% Off
Pros
- Works for casual and formal occasions
- Lightweight responsive cushioning
- Available in 10 colorways
- Outsole with high-traction rubber pods at toe and heel
Cons
- May have to be worn with thicker sock
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
Now 13% Off
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
Now 20% Off
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 |
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Most Comfortable Plain Toe Dress Shoe
Johnston & Murphy Upton Plain Toe Dark Brown Nubuck
Pros
- Water-resistant construction
- Breathable mesh lining to keep your feet cool
- Can be dressed up or dressed down
Cons
- Size runs a little big
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.
| Sizes | 8—13 |
|---|---|
| Fit | Medium |
| Colors | Brown nubuck, gray nubuck, white nubuck, black leather, brown leather, and tan leather |
| Upper material | Leather |
| Sole material | TruFoam EVA Composite |
Most Comfortable Loafers
G.H. Bass Larson Suede EVA Weejuns Loafer
Now 52% Off
Pros
- Under $100
- Silhouette never goes out of style
- Easy to put on and slip off
Cons
- Better option for wider feet
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.
| Sizes | 7—13 |
|---|---|
| Fit | Medium |
| Colors | Denim, sage, and desert sand |
| Upper Material | Suede |
| Sole Material | EVA |
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 |
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Most Comfortable Casual Dress Shoe
Allen Edmonds William Wingtip Derby
Now 47% Off
Pros
- 360º bench welt construction for durability
- Timeless style
- Comes in leather and suede options
Cons
- Only a couple color options for both upper materials
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.
| Sizes | 7—14 |
|---|---|
| Fit | Medium |
| Colors | Walnut leather, dark brown leather, bone suede, and denim suede |
| Upper Material | Leather or suede |
| Sole Material | XL Extralight® |
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
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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 |
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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.
Read More About the Most Comfortable Shoes to Buy Now
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Read More About the Best Dress Clothes to Buy Now
Best Dress Shirts for Men | Best White Dress Shirts | Best Suits for Men | Best Blazers for Men | Cocktail Attire for Men
