Best Overall Comfortable Dress Shoe
Ecco Citytray Cap Toe
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 Only comes in two colors
Ecco landed the top spot on the list because the Citytray Cap Toe does an excellent job of concealing all the comfortable upgrades and keeping the appearance of 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 footbed liner on the inside. This little detail has the additional benefit of molding to your foot over time.
Ecco’s Citrytray midsole and outsole system provides the kind of traction and stability you find in a walking shoe. We tested it for over ten hours of continuous wear and the support held strong, minimizing foot fatigue. This will keep your dogs happy at work, on wedding dance floors, and any time you’re on the move.
Above all, this looks like a dress shoe that every man should have in his arsenal. A simple cap toe derby in brown or black works for absolutely every occasion, from casual to black tie. There is just enough detail to not be boring, but nothing that can clash with any possible look. One of the most comfortable, stylish, and useful shoes we’ve ever tested, full stop.
Read more: Best Men’s Leather Sneakers
Fit Medium Colors Brown and black Upper Leather Sole Rubber
Most Flexible Comfortable Dress Shoe
Cole Haan GrandFlex Dress Cap Toe Oxfords
Pros Segmented outsole provides flex where it is needed most Outsole texture has strong grip The heel block is shock absorbing Cons No ankle padding can cause some friction points
When it comes to outsole design, this was the most interesting and functional shoe that we tested. Cole Haan was one of the first brands to put rubber sneaker-inspired soles on leather dress shoes, and the American shoemaker continues to stay ahead of the curve in that field. The outsole has been broken into segments between the arch and toes. This provided exceptional flex where it is needed most, while keeping the heel and arch strong and supportive. It was very effective at taking pressure off the balls of our feet in testing.
Our style editors appreciate how this super functional outsole system doesn’t look too sporty or funky. It has the appearance of a standard dress shoe until you look closely. Adding sneaker-like comfort without making a dress shoe look too much like a sneaker has been the biggest challenge for comfortable dress shoes in the past, and we think Cole Haan nailed it here.
Fit Medium Colors Brown, burgundy, black Upper Leather Sole Rubber
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Best Affordable Comfortable Dress Shoe
Rockport DresSports 2 Go Plain Toe Shoe
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. Our testers found that it feels and wears more like a leather sneaker than a dress shoe, which a testament to the overall comfort.
The all white sole contrasts nicely with the brown or black upper to create a business causal look. These are great work shoes for the more relaxed office dress codes out there today. Our style editors found that chinos of any color are a perfect match for this shoe.
Fit Medium Colors Caramel and black Upper Leather Sole Rubber
Most Comfortable Loafer Dress Shoe
G.H. Bass Easy Brush Off Weejuns Loeafer
Pros Fully rubber outsole for enhanced flexibility Leather footbed molds to your foot over time Wide open upper increases airflow to your foot Cons Upper and footbed take some time to break in
G.H. Bass grabbed top honors on our Best Loafers list with the original Weejuns Loafer. Even though that version is very comfortable, the Maine shoemaker offers an even cozier version equipped with a fully rubber midsole. The result is a noticeably more flexible walking experience, which eased some pressure on our arches and balls of our feet. Another significant advantage rubber has over leather is that it skips the breaking-in period, at least for the outsole.
Up top, this Weejun loafer is identical to the original. You get the same high quality leather, impressive craftsmanship, and timeless look that won over Fashion Director Ted Stafford. One thing to note is that the leather footbed will feel stiff at first, but it will mold to your foot as it breaks in, eventually creating a customized feel that cradles the button of your foot.
Fit Medium Colors Burgundy Upper Leather Sole Rubber
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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.
Fit Standard Colors 12 options to choose from Upper Leather or suede Sole Thermoplastic polyurethane
Best Comfortable Dress Shoe for a Suit
Nunn Bush Centro Flex Cap Toe Oxford
Pros Smooth toe cap design Removeable insoles Stitched down sole construction Cons Can run a little too long and narrow
This may look like a standard issue cap toe oxford shoe, 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.
The Milwaukee based shoemaker has been in operation for over a century. Our style editors appreciate that this oxford is true to the same classic look that the brand has made for generations. Only, now it is bolstered with supportive features. Of all the shoes on this list, we found that this one works best with a suit because of that timeless look.
Fit Medium and Wide Colors Black, brown, and cognac Upper Leather Sole Synthetic rubber
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Most Comfortable Off-Hours Dress Shoes
Nisolo Rey Everyday Derby
Pros Wide toe box allows for a natural toe splay Natural leather upper is breathable and flexible Grip all along the entire outsole
Upgrade your everyday footwear game with this exceptionally comfortable derby from Nisolo. Sure, it is a fully functional dress shoe, but we think that the Rey Everyday Derby looks best with jeans and a t-shirt. The natural leather finish doesn’t have that shiny look that comes with polished dress shoes. It resembles a plain-toe boot and styles in much the same way. Our style editors think it goes best with flannel button downs, oxford shirts, and crewneck sweatshirts.
Rather than injecting innovative designs, Nisolo achieved top level comfort in this derby by keeping things light and simple. The leather isn’t excessively treated, so it retains a supple flexibility and breathability inherent to cow hide. Plenty of room in the wide toe box and mid-foot allowed us to slip the shoe on and off with ease. We found a strong emphasis on arch support in the leather and rubber sole design.
Fit Medium Color Tobacco, brown, black Upper Leather Sole Leather and rubber
Most Comfortable Wide Dress Shoe
Florsheim Rucci
Pros Old fashioned wingtip look Strong grip outsole Flexible leather upper Cons Opening is a little tight for getting on and off
Florsheim makes classic looking dress shoes feel comfortable by paying special attention to all three layers of the sole. Starting on the inside, the custom designed insole struck just the right balance between squishy and firm. The rubber midsole looks like leather but felt flexible and provided strong arch support. We felt sure footed the whole time with the grippy outsole. After spending a few hours in this dress shoe, we could feel the entire sole stack working together to provide support and comfort.
Wide fit dress shoes are not easy to come by. Really good looking wide fit dress shoes are even more of a challenge. This is hands down the most comfortable dress shoe that we tested for guys with wide feet, and the old school wingtip upper is perfect for formal occasions and weekday office attire.
Fit Medium, wide Color Light brown, black, dark brown Upper Leather Sole Rubber
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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.
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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.
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