The most comfortable men’s dress shoes are the formal(ish) ones you wear to work, weddings and parties when sneakers won’t fly. As is the case with many types of shoes, there are good and bad ones out there. The wrong dress shoes are stiff, painful to wear and look like they belong in a time capsule from the 1950s. The best dress shoes, on the other hand, mold to your feet, feel great and fit in with other stylish items in your closet. To find out what separates the torturous from the truly excellent, we consulted experts who spend a lot of time on their feet and prioritize comfort (and good looks) in footwear.
Ahead, you’ll find all the pairs we highly recommend. Our picks for the Most Comfortable Men’s Dress Shoes Overall (the Allen Edmonds Park Avenue Cap Toe Oxford) and Most Affordable Comfortable Men’s Dress Shoes (the Johnston & Murphy Lewis Plain Toe) not only have outfit-making potential, but they’re also nearly as comfortable as your everyday sneakers. You can read more about how we made these selections at the end of this guide, and for more on men’s fashion, check out our stories on best men’s dress shirts and best men’s jeans.
Most Comfortable Men’s Dress Shoes Overall
Supreme, Sartorial Comfort
This classic shoe—first introduced in 1982—is frequently touted by both stylists and podiatrists due to its sleek silhouette and supportive fit. While so many comfortable dress shoes skew vaguely orthopedic, this iconic lace-up oxford is cushy and forgiving yet visually minimalist: It features an updated low profile, leather-lined interior, cork insoles that mold to your foot and it’s available in ten different widths.
Most Affordable Comfortable Men’s Dress Shoes
Cushioned Style For A Modest Price
This more casual dress shoe has a memory foam-cushioned footbed to make it springy, and the rubber sole offers traction while commuting across cement-lined streets, subway platforms, or on slick office flooring. While this shoe only comes in a medium width, it’s a little more forgiving than other, stiffer shoes and it runs slightly wider in the forefoot for added comfort, according to Howard Friedman, MD, podiatrist at Suffern Podiatry.
Most Comfortable Men’s Dress Boots
Ankle Boots With Comfortable Soles
British shoe manufacturer Crockett and Jones has been making men’s footwear since 1879, with designs ranging from sporty chukka boots to elegant velvet slippers to versatile derbys. This pull-on pair’s almond-shaped toe allows feet room to spread out, and its water-resistant welt and cleated Vibram rubber sole make it springy, durable and the perfect traction for slick winter sidewalks.
Most Comfortable Men’s Business Casual Shoes
Understated, Casual Cool
Luxury Italian shoemaker Santoni is possibly best known for their handmade high-end oxfords and derbys, which are boardroom favorites. This casual take on a classic—it’s an elegant sneaker-derby hybrid—can be worn with everything from dress pants to khakis to jeans. While these shoes have a slightly tapered shape, some say they run large so take that into consideration when picking your size.
Most Comfortable Men’s Dress Shoes For Standing All Day
Elevated Shoe With Cushion And Flexibility
Cole Haan is at the top of foot specialists’ lists for comfort, and this pair has hundreds of positive reviews. While the fabric construction is slightly informal, the tight weave is more sophisticated than a sneaker and the responsive material allows feet and toes room to spread out. The special soles have pumped up cushioning, foot-friendly flexibility and they’re lightweight. Another bonus: These offer a great fit and comfort right out of the box.
Most Comfortable Men’s Slip-On Dress Shoes
Extreme Comfort From A Luxury Brand
These unassuming, hand-stitched slip-ons are so popular it can be difficult to get your hands on a pair. Their low-profile white sole is springy and forgiving on feet and joints, and the supple full-grain leather is flexible if you’ll be doing lots of walking. We especially love that the sneaker-meets-dress-shoe construction makes them appropriate for a variety of outfit choices—paired with khakis, slightly rolled jeans or stylish suiting.