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

Best Overall Comfortable Dress Shoe

Ecco Citytray Cap Toe

Best Overall Comfortable Dress Shoe

Ecco Citytray Cap Toe

Now 25% Off

ConsComes 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.

Sizes6—13FitMediumColorsBrown and blackUpper MaterialLeatherSole MaterialRubber

Most Comfortable Business Casual Dress Shoes

Amberjack The Original

Most Comfortable Business Casual Dress Shoes

Amberjack The Original

ConsMay 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.

Sizes7—15FitStandardColors12 options to choose fromUpper MaterialLeather or suedeSole MaterialThermoplastic polyurethane

Most Affordable Comfortable Dress Shoe

Rockport DresSports 2 Go Plain Toe Shoe

Most Affordable Comfortable Dress Shoe

Rockport DresSports 2 Go Plain Toe Shoe

Now 33% Off

ConsOnly 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

Sizes7—15FitMediumColorsCaramel and blackUpper MaterialLeatherSole MaterialRubber

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Most Comfortable Wingtip Dress Shoe

Cole Haan ØriginalGrand Wingtip Oxford

Most Comfortable Wingtip Dress Shoe

Cole Haan ØriginalGrand Wingtip Oxford

Now 24% Off

ConsMay 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.

Sizes7—16FitMedium and WideColorsBlack/white, brown/white, brown/dark brown, black/black, gray/white, and oxblood/blackUpper MaterialLeatherSole MaterialRubber

Most Comfortable Slip On Dress Shoe

Florsheim Hamptons Moc Toe Venetian Loafer

Most Comfortable Slip On Dress Shoe

Florsheim Hamptons Moc Toe Venetian Loafer

Now 13% Off

ConsNot 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.

Sizes7—14FitMedium and WideColorsGray, black, cognac, brown, tan, navy, and blueUpper MaterialLeather or suedeSole MaterialRubber

Most Comfortable Cap Toe Dress Shoe

Nunn Bush Centro Flex Cap Toe Oxford

Most Comfortable Cap Toe Dress Shoe

Nunn Bush Centro Flex Cap Toe Oxford

Now 20% Off

ConsOne 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.

Sizes7—14FitMedium and WideColorsBlack, brown, and cognac Upper MaterialLeatherSole MaterialSynthetic rubber

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Most Comfortable Plain Toe Dress Shoe

Johnston & Murphy Upton Plain Toe Dark Brown Nubuck

Most Comfortable Plain Toe Dress Shoe

Johnston & Murphy Upton Plain Toe Dark Brown Nubuck

Now 13% Off

ConsSize 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.

Sizes8—13FitMediumColorsBrown nubuck, gray nubuck, white nubuck, black leather, brown leather, and tan leatherUpper materialLeatherSole materialTruFoam EVA Composite

Most Comfortable Loafers

G.H. Bass Larson Suede EVA Weejuns Loafer

Most Comfortable Loafers

G.H. Bass Larson Suede EVA Weejuns Loafer

ConsBetter 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.

Sizes7—13FitMediumColorsDenim, sage, and desert sandUpper MaterialSuedeSole MaterialEVA

Most Comfortable Dress Boots

Astorflex Bitflex Chelsea Boot

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