The Most Comfortable Dress Shoes for Men You’ll Actually Want to Wear

Wolf & Shepherd Crossover™ Longwing
Courtesy of Wolf & Shepherd
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As the world waxes and wanes with the idea of going back to normal, we’ve been sprinkled with formal-ish settings like on and off days in the office and one-off weddings folks pushed from 2020 to 2021. While fashion has really toned down in the past couple of years in terms of formality, we’re still keeping our best dress shoes on deck in case we need them for situations like the ones mentioned earlier. But, when dressing up no matter the occasion, you don’t want to be in pain. That’s why we believe that the best dress shoes for men double as the most comfortable dress shoes you can purchase now.

When seeking out the most comfortable dress shoes for men online, you want to get down to the science of that description. If the site you’re on foregoes any talk regarding the sole of the dress shoe, don’t even bother with the buy button. It’s not worth it even if it’s the coolest dress shoe you’ve ever seen. Ensure that the description mentions comfortable soles with bonus points if it mentions an EVA (ethylene-vinyl acetate) footbed.

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When you’re wearing dress shoes, there’s a solid chance you’re going to be spending the majority of the time moving. Whether you’re walking around the office, commuting to work or doing the Electric Slide on the dancefloor at Bob and Karen’s wedding, comfort is key through and through.

To make your life easier, we went on a hunt for the most comfortable dress shoes men can wear in 2021. Check out our favorites below.

1. Cole Haan ØriginalGrand Wingtip Oxford


Cole Haan has mastered the art of comfortable dress shoes. And, not to mention, they’re quite handsome. These stellar-looking wingtip oxfords are drenched in a leather upper that can be chosen in a variety of handsome colors. They’re built with an EVA midsole and a rubber outsole to ensure that no matter how many steps you take, your feet won’t be in any pain. That’s not all though, to top it all off, these shoes are cushioned with Grand.ØS technology (a Cole Haan specialty) that will keep your soles ready for more movement.

Cole Haan ØriginalGrand Wingtip Oxford, most comfortable dress shoes Courtesy of Cole Haan

Cole Haan ØriginalGrand Wingtip Oxford



2. Dr. Scholl’s Sync Oxford


You should already know by the name Dr. Scholl that these are going to feel like clouds on your feet. These faux leather oxfords utilize BE FREE Energy technology in the insole with three different zones to push comfort to the max. Each shoe has extra support near the toes, high recovery foam at the ball and dense foam cradling at the heel for each part of the foot’s specific needs. Plus just look at how handsome these oxfords are. You can’t go wrong.

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Dr. Scholl's Sync Oxford, most comfortable dress shoes Courtesy of Amazon

Dr. Scholl's Sync Oxford



3. Johnston & Murphy Waterproof XC4® Casual Dress Plain Toe Sneaker


We’ve all been there. You’re walking outside of the house about to hop on the train when a drop of rain hits the tip of your nose. It’s about to downpour. Comfortable dress shoes can only go so far when it comes to keeping you cozy, meaning the majority when wet will have you SOL. Thankfully, that isn’t the case with Johnston & Murphy’s plain toe sneakers. These waterproof bad boys will keep your feet dry no matter what the case may be. Complete with the magic EVA midsole, you’re all set with these ones.

Johnston & Murphy Waterproof XC4® Casual Dress Plain Toe Sneaker Courtesy of Zappos

Johnston & Murphy Waterproof XC4® Casual Dress Plain Toe Sneaker



4. Clarks Un Tailor Tie


These have that same look you’re familiar with in a pair of oxfords. No gimmicks, no tricks, just a stylish, comfortable dress shoe for men. It’s got a shiny leather upper that will keep you looking handsome and a dual density Ortholite® footbed with a rebound EVA sole to ensure very step you take will keep you wanting to walk further. For added comfort, each oxford is complete with a reinforced toe and heel pad that absorbs any shock and produces energy.

Clarks Un Tailor Tie, most comfortable dress shoes Courtesy of Zappos

Clarks Un Tailor Tie



5. Cole Haan ØriginalGrand Energy Twin Oxford


Although the majority of comfortable dress shoes should stick to more neutral tones that match with just about whatever, a pop of color never hurt anybody. Cole Haan’s ØriginalGrand Energy Twin Oxford hit the nail on the head by pairing a classic color and design with the subtle energy we want to see in a shoe. It’s got a leather upper with a moisture-wicking lining to kiss sweaty feet goodbye. The shoe is complete rebound technology to combat shock, return energy and cushion your foot correctly. Bottomed out with a slight neon green? It’s going to be a yes from us.

Read More: The Most Comfortable Sneakers

Cole Haan ØriginalGrand Energy Twin Oxford, most comfortable dress shoes Courtesy of Cole Haan

Cole Haan ØriginalGrand Energy Twin Oxford



6. TOMS Navi Dress Shoe


You know TOMS, don’t you? The company that donates a pair of shoes to someone in need with every purchase? Well, they make comfortable dress shoes, too. These Navi Dress Shoes are made with a suede and leather upper to ensure a handsome look all day long. Walking around a lot? Good. These TOMS have an OrthoLite® Eco X40 insole to cushion your foot no matter how far you go. To top it all off, these dress shoes are completely made with plant derivative and recycled materials.

TOMS Navi Dress Shoe Courtesy of TOMS

TOMS Navi Dress Shoe



7. Wolf & Shepherd Crossover™ Longwing


Italian leather? Come on. It doesn’t get any more dapper than that. With a full-grain Italian calfskin upper and an uber soft, abrasion-resistant sheepskin lining, these longwings will have you feeling like you’re roaming around the streets of Rome in the world’s finest outerwear. Not only are they striking, but they’re complete with a memory foam footbed with industry-leading comfort for miles and miles of walking.

Wolf & Shepherd Crossover™ Longwing Courtesy of Wolf & Shepherd

Wolf & Shepherd Crossover™ Longwing



8. Thursday Boot Captain Boot


These boots are made for walking and that’s just what they’ll do. We’re big fans of Thursday Boot here at SPY, so don’t be so shocked that we’re naming the Captain boot one of the most comfortable dress shoes. Because, yes, boots can be dress shoes. These are some of the most handsome, durably made and comfortable boots we’ve ever come across. They have cork-bed midsoles that form to your feet over time and a DuraEVA comfort strip that keep your feet feeling extra cozy. You can also easily dress these up or down.

Read More: Best Men’s Boots

Thursday Boot Captain Boot, most comfortable dress shoes Courtesy of Thursday Boot

Thursday Boot Captain Boot



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