11 Of The Best Dress Shoes That Feel Like Sneakers in 2023

Many of the most popular styles of dress shoes have very specific silhouettes. Aesthetics play a key role in their construction, and unfortunately, sometimes comfort takes a back seat. So when we start talking about dress shoes that feel like sneakers, we need to take a few things into consideration. The biggie: They’re going to look like dress shoes, but not entirely like dress shoes.

Maximum comfort sometimes comes at the expense of maximum style. That said, I’ve done my best to avoid the cringiest of men’s dress shoes that feel like sneakers. Cushy soles, leather liners, and arch supports await. They’re not sexy, but they’re a few crucial elements that make up this list of the best dress shoes that feel like sneakers.

Key Takeaways 

The best dress shoes that feel like sneakers are not only the ones you can wear to any occasion, they also put plenty of emphasis on comfortable construction.

The Allen Edmonds Park Avenue Oxford is arguably the gold standard of sneaker-like comfort hidden within an elegant dress shoe. It’s also on the higher end, price-wise. So an excellent budget option can be found in Dockers’ Gordon Oxford.

Since its inception in 1922, Allen Edmonds has been setting the bar for comfort and quality craftsmanship in men’s dress shoes. The storied shoe company supplied shoes to the U.S. Navy and Army during World War II, and its shoes have been worn by multiple US presidents.

Pedigree: check.

If you’re intrigued but also annoyed by all that shameless name-dropping, I get it. Comfort. You’re here for comfort. And you’ll find plenty of it in the Allen Edmonds’ Park Avenue Cap-Toe Oxford. The vegetable-tanned leather soles and the leather-lined interior of the shoe are a nice start, but the comfort is taken to the next level by its cork insoles. Over time, they meld to the shape of your feet, and cork is known to help reduce joint stress.

Material: 100% Leather | Colors: 6 | Sizes: 5-16 | Toe Style: Round

If the Allen Edmonds Park Avenue is an Aston Martin, the Dockers Gordon is, let’s say, a Honda Accord. They’re both great cars, but the latter is all about high function (with just enough form thrown in for good measure).

The full-grain leather is soft and cushy, and the padded collar of the shoe won’t cut into your ankles like some other dress shoes tend to. Oh, and fun fact: The American Podiatric Medical Association has given the Gordon its seal of acceptance for overall quality and its promotion of good foot health. Not to be confused with the J.D. Power dependability award.

Material: 100% Leather | Colors: 2 | Sizes: 7-17 | Toe Style: Round

This is truly a dress shoe for the outdoorsman who isn’t willing to sacrifice style while out on adventures. A derby that’s business up top, party on the bottom. The calfskin leather upper moves in lockstep with the motion of your feet, and the para sole is light and flexible.

One thing you probably noticed the second you laid eyes on this guy is that it’s definitely not the type of shoe that’s going to be right for everyone. You’re dealing with a pretty specific look here, meaning the Oreves is probably best left to the great outdoors.

Material: 100% Leather | Colors: 3 | Sizes: 5-14 | Toe Style: Round

Classic styling. Masculine elegance. Goodyear welted. Morjas spent a lot of time and effort making sure you have a stylish and comfortable pair of penny loafers to walk around in.

The front of the shoe is designed to be roomy enough to give your toes some breathing room, while the fit snugs up a bit around the heel and waist. The result is a shoe that just feels right.

And thanks to that Goodyear welt, this is a heritage pair of shoes that’ll be with you as long as you’d like them to be. Wear them sockless with jeans. Dress them up with a summer suit. There are no wrong turns with this timelessly handsome pair of loafers.

Material: 100% Leather | Colors: 5 | Sizes: 5.5-13.5 | Toe Style: Round

Now, could I have chosen a dressier slip-on for this category? Yes, there are so many quality options out there that are more formal in the traditional sense. I trust you’ll have no trouble finding them if that’s what you’re looking for.

As for Cariuma’s IBI slip-on, I’m thinking more expert-level summer vibes. The kind of crisp white slip-on made of bamboo and recycled materials that the confident man can wear with a linen shirt and pants or a high-waisted pair of shorts with a button-down. Either way, the memory foam, cork and Mamona oil insoles, and breathable uppers are going to keep your feet feeling light as air.

Material: Bamboo & Recycled PET | Colors: 9 | Sizes: 5-13 | Toe Style: Round

When the company was founded in Brooklyn in 2015, Amberjack received a ton of buzz from major print and digital publications. The hype has since fizzled out a bit, but broad interest in the company’s shoes has yet to wane—especially in the case of The Original.

The arch support integrated into the sole is heat-activated and acts like a more durable version of memory foam for conforming to your feet. Elsewhere on the comfort front, the inside of the shoe is lined with sheepskin, and the outer is made of supple full-grain leather that comes in 11 colors (I’m a fan of walnut and the other classic shades of brown). As far as dress shoes that feel like sneakers go, this one may as well have written the book.

Material: 100% Leather | Colors: 11 | Sizes: 7-13 | Toe Style: Round

Alright, hear me out. Yes, this looks like the shoe version of a ‘90s hovercraft. But this happens to be an article about dress shoes that feel like sneakers and, well… this is one of them. The Cole Haan Zerogrand Wingtip is one of the top-rated oxfords on Amazon when it comes to comfort.

These shoes feature EVA midsoles, which are commonly used in sneakers to help absorb shock and create a softer, bouncier feel. Meanwhile, the rubber outsole puts even more icing on the comfort cake. It’s available in 23 colors, but I’d recommend avoiding the ones that draw too much attention to the soles if you want to maintain a modicum of sartorial respect for yourself.

Material: 100% Leather | Colors: 22 | Sizes: 6.5-16 | Toe Style: Round

In the budget corner, Clarks picks up where other dress shoes that feel like sneakers leave off. The Tilden’s popularity can be attributed to a number of features—the OrthoLite footbed provides breathability and extra cushion, for example, while the thermoplastic rubber soles keep your feet light and airy as they bounce off the ground.

The oxford is already a versatile style of shoe, and the Tilden’s emphasis on comfort makes it that much more so. The stitching and detailing aren’t much to write home about, but you’ll be good to go if you stick with black for this one. Regardless, this is a shoe that you can stand in all day without breaking a sweat.

Material: 100% Leather | Colors: 10 | Sizes: 7-15 | Toe Style: Square

Bruno Marc is known for making some of the most comfortable dress shoes that feel like sneakers on the market. These aren’t traditional monk strap shoes in terms of design and aesthetic, but if you’re searching for a monk strap-adjacent pair of shoes that you can stand in all day or wear from your morning coffee to happy hour, this is one of your best bets.

The cushioned latex insole is forgiving and molds to the contours of your feet over time, and the thermoplastic elastometers sole is better for both the environment and your feet. The outer is synthetic, which helps keep the price point low, but you’re working with a cozy leather lining on the inside where it counts.

Material: 100% Synthetic | Colors: 8 | Sizes: 6.5-13 | Toe Style: Square

Florsheim has been around since 1892 and has sold countless pairs of shoes since then. Though the quality can vary wildly from shoe to shoe, the Midtown Cap Toe Oxford is a nice middle point in terms of price and craftsmanship. More importantly, almost every aspect of the shoe was made with comfort in mind.

The cushioned footbed features Ortholite high rebound foam that hugs your feet around the perimeter of the shoe. And around the ankles—a familiar pain point for anyone who’s worn dress shoes for a longer period of time—there’s a padded collar to reduce blisters and painful rubbing. Leather upper. Rubber sole. Handsome, timeless styling. Check, check, and check.

Material: 100% Leather | Colors: 4 | Sizes: 7-18 | Toe Style: Almond

The James from Cobbler Union is made by hand in Spain by skilled craftsmen and craftswomen, and that attention to detail shines throughout. This is a Goodyear welted pair of shoes with rubber soles that mimic sneakers in weight and feel. The inner lining is full-grain calfskin leather to keep things pillowy soft on the inside as well.

The design is very much a classic that would look fantastic with a suit at a formal occasion or sitting below a crisp pair of dark jeans and a smart shirt or sweater.

Material: Full-grain leather | Colors: 2 | Sizes: 7-13 | Toe Style: Round

What To Look For When Buying Dress Shoes That Feel Like Sneakers

Comfort

It seems so obvious, but when you’re looking for men’s dress shoes that feel like sneakers, you need to be looking for a few key comfort indicators. The insoles should be made of shock-absorbent materials that mold to your feet, there should be some type of padding around the ankle area, the lining should be breathable and cozy. Finally, opt for sneaker-like rubber soles.

Style

Footwear styles for men run the gamut. You’ve got your ruggedly elevated dress boots. Your tricky-but-worth-it dress sneakers and plenty of others. But if you’re looking for a versatile pair that you can wear to almost any occasion, stick to Oxfords, loafers, and derbys.

Material Composition

When you start getting into dress shoes that feel like sneakers, you’ll find that materials tend to stray a bit from those you’d typically find for traditional dress shoes. If possible, look for options with 100% leather uppers that offer superior comfort while breaking in and conforming to your feet over time. Durable rubber soles are also ideal if you plan on frequently wearing the shoes while on your feet.

Final Verdict 

Coming in on top in terms of dress shoes that wear like sneakers is the legendary Park Avenue from Allen Edmonds. Its cork insoles, leather lining, and durable soles are a few key comfort indicators that you’ll want to look for in this type of dress shoe.