10 Best dress shoes that will feel like sneakers by 2023

Dress shoes come in a variety of shapes and sizes. The aesthetics of dress shoes are important, and comfort can sometimes be overlooked. When we talk about dress shoes that are more like sneakers, there are a few factors to consider. The biggie: They’re going to look like dress shoes, but not You can find out more about it here. Dress shoes are a good example.

Sometimes, maximum comfort comes at the cost of maximum style. That said, I’ve done my best to avoid the cringiest of men’s dress shoes that feel like sneakers. The padded soles, leather liners, arch supports, and leather linings are waiting for you. 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.

The Key Takeaways 

Not only are they comfortable, but the best dress sneakers that feel like sneakers can be worn to any occasion.

The Allen Edmonds Park Avenue Oxford has arguably set the standard for sneaker comfort in a stylish 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, embodying the essence of what it means to “look like a dress shoe, feel like a sneaker.” 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 leather lining, the vegetable-tanned leather and the leather soles are all great features. However, the insoles made of cork take the comfort level to another level. Cork insoles are known to reduce stress on joints and they adapt over time to the shape of feet.

Material: 100% Leather Toe Style: | Colors: 6 | Sizes: 5-16 | 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 upper is made of calfskin and moves with your foot. The para sole, which is flexible and light, follows the movement.

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% LeatherToe Style | Colors: 3 | Sizes: 5-14 | Toe Style: Round

Classic styling Masculine elegance. The heel stack is made of premium leather with a partial rubber cap for great traction. The Jacket Maker took a lot time to make sure that you get a comfortable and stylish pair of penny loafers.

The fit is snug around the heel, but the front of the shoe has enough room for your toes to breathe. Much of this is owed to the style of stitching The Jacket Maker employs – the Blake stitched construction. This construction allows the shoe to be lightweight and flexible, resulting in a comfortable ride straight out of the package.

The end result is an all-around comfortable shoe. Wear them with jeans sockless. Dress them up in a summer suit. With this pair of handsome loafers, you can’t go wrong.

Material: 100% Leather Toe Style: | Colors: 5 | Sizes: 7-14.5 | Toe Style: Round

Could I have selected a more formal slip-on in this category? There are many options that are 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. A pair of clean, white slip-ons made from bamboo and recycled materials. The confident man will wear them with a linen shirt with pants or high-waisted pairs of shorts with button-down shirts. Memory foam, Mamona oil and cork insoles will keep your feet as light as air. Toe Style

Material: Bamboo & Recycled PET | Colors: 9 | Sizes: 5-13 | 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. It’s a fun fact that the American Podiatric Medical Association gave the Gordon their seal of approval for its overall quality, as well as its promotion of foot health. The J.D. is not to be confused. Award for power reliability.

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

Listen to me. 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, or what some might call athletic dress shoes, and, well… this is one of them. Cole Haan Zerogrand Wingtips are one of the most comfortable oxfords available on Amazon.

These shoes have EVA midsoles. They are often used in sneakers for shock absorption and to give a more bouncy, soft feel. Rubber outsoles add to the comfort. 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 Toe Style: | Colors: 22 | Sizes: 6.5-16 | Toe Style: Round

Clarks is a budget-friendly option that picks up from other dress shoes which feel like sneakers. 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. You can stand all day in this shoe without getting hot.

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

Bruno Marc makes some of the most comfortable shoes on the market that are similar to sneakers. 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 thermoplastic elastometers outsole is both better for the environment and for your feet. Cushioned latex is used in the insole, which molds over time to your foot’s contours. Toe Style: 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 is a company that has been in business since 1892. They have sold thousands of pairs of shoes. Midtown Cap Toe Oxford, a shoe that is both affordable and well-made, offers a nice compromise in terms of quality. Most importantly, the shoe was designed with comfort as a priority.

The Ortholite high rebound footbed hugs your toes all around 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 Elegant, timeless styling. Check, check, check.

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

Amberjack was a big hit when it launched in Brooklyn, New York in 2015. Print and digital media were enthralled by the new company. 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 is heat activated and works like a durable version of memory-foam to conform 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). This shoe is the best dress shoe that feels like sneakers.

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

The James from Cobbler Union are made in Spain, by skilled craftsmen. This attention to details is evident throughout. The rubber soles are similar to sneakers, both in weight and feeling. The inner lining of the shoes is made from full-grain, soft calfskin.

This design is a true classic. It would look great with a suit for a formal event or paired with dark jeans, a smart sweater or shirt and crisp dark denim.

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

Dress Shoes that Feel Like Sneakers: What to Look Out for

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 must be made of materials that are shock-absorbing and mold to your foot. They should have padding around the area of the ankle, while the linings should be soft, breathable, and comfortable. Last but not least, choose rubber soles similar to those of sneakers.

Style

Men’s footwear styles are diverse. You’ve got your ruggedly elevated dress boots. Dress sneakers that are worth the effort and many 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. When possible, choose options that have 100% leather uppers. They will offer you superior comfort as they break in and adapt to your feet with time. If you are planning to wear the shoes on your feet a lot, durable rubber soles will also be ideal.

Final Verdict 

Allen Edmonds’ legendary Park Avenue dress shoe is the best option for those looking for shoes that look and feel like sneakers. 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.