19 Stylish & Comfortable Dress Shoes That Feel Like Sneakers

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It doesn’t take a genius to understand why guys would want to find dress shoes that feel like sneakers. 

Around here we like to say that shoes are the secret weapon of style: 

A sharp-looking pair of dress shoes can elevate your look to the next level, while the wrong pair – or worse, foregoing dress shoes altogether – can significantly dampen your dapperness. 

Unfortunately, while dress shoes can significantly enhance your handsomeness, they can also wreak havoc on your feet, back and posture, especially if you’re on your feet for much of the day.

Sometimes they can even be downright painful, causing blisters or creating an acute foot pain in your arches. 

Fortunately, shoe manufacturers have (finally) gotten wise to the problem, and have started manufacturing shoes that combine the style and class of traditional dress shoes with the support and comfort of sneakers.  

Whether you’re looking for sneakers that look like dress shoes or dress shoes that feel like sneakers, in this post I’ve rounded up more than a dozen different styles that will keep you both well appointed and well supported.

Look Sharp, Stroll Soft:

The (Absolute) Best Dress Shoes That Feel Like Sneakers

Breaking Down the Best Dress Shoes with Sneaker Soles
Overall Best Dress Shoes That Feel Like Sneakers ↓

Wolf & Shepherd 

Crossover™ Longwing

Wolf and Shepherd Crossover™ Longwing
  • 4.8 Stars
    • 421 Reviews

Founded by former decathlete Justin Schneider, Wolf & Shepherd’s entire reason for being is to infuse “athletic comfort and technology” into dress shoes, loafers and other stylish models.

Their Crossover Longwing model is damn near the perfect pair of shoes, combining a smooth leather upper made from full-grain Italian calfskin with a comfortable rubber outsole.

Plus, they also come with a removable memory foam footbed, just to up the comfort ante a little further.

From the top these look like sharp and stylish dress shoes (I love the toe design and simplicity of the leather), but the cushioned insole down below means you can go all day without worrying about any discomfort.

Promising Review:

I was hesitant at first purchasing a dress shoe that looked more in the casual family, but after wearing them the first time I fell in love with the comfort and look of them as well.

Possibly the most comfortable dress shoe I have ever put on my feet, and will certainly own more pairs moving forward!

– Robert S.

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The Original

Amberjack Originals
  • 4.9 Stars
    • 151 Ratings 

Amberjack’s flagship Originals are premium leather dress shoes chock full of comfort features.  

The A-grade full grain leather upper gives the shoes a distinct touch of class that can pass muster in offices with strict dress codes. 

But the two layers below it are built for comfort. 

The midsole features a durable form of memory foam that provides heat-activated arch support triggered by your body heat, while the dual-density outsole combines the flexibility of athletic shoes with the support of hiking boots. 

What’s nice about these ones is that they have a relatively low heel when compared to some of the other shoes on this list, making them a little sleeker without sacrificing comfort. 

The result is a classic-looking pair of comfortable men’s dress shoes you can wear damn near anywhere. 

Promising Review: 

These shoes are immensely comfortable right out of the box. I have arthritis in my knees. With these shoes there is markedly less pain as I walk. I have already ordered a second pair. 

– Arthur H.

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Cole Haan

ØriginalGrand Wingtip Oxford

Cole Haan ØriginalGrand Wingtip Oxford
  • 4.8 Stars
    • 681 Ratings 

Long known for their comfy and high quality shoes, Cole Haan makes some of the best men’s dress shoes and dress boots. 

So it’s no surprise that their ØriginalGrand wingtips are not only one of the best looking pairs of shoes on the market today, but one of the most comfortable.

They combine a buttery leather upper – available in six colors – with an EVA midsole and rubber outsole that provides responsive cushioning and natural flexibility when you’re on the move. 

Promising Review: 

These Cole Haan shoes are excellent. They are lightweight, fashionable, and well made. Though they are light, they are as sturdy as my Allen Edmonds. 

At my daughter’s wedding two weeks ago, I wore them from 2 pm to 5 am, and my feet never complained. And my daughter complimented me on my footwear!

I am now a fan of Coe Haan, and look forward to my next pair.

– John A.

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Atticus LTLace

Clark’s Atticus LTLace
  • 5 Stars
    • 1 Rating 

Clark’s Atticus oxford is an excellent blend of style and comfort that hardly looks like a comfort shoe.  

The thin (by comfort-shoe standards) rubber soles boast dual-density foam technology that will keep your feet padded all day, while the medal-rated leather upper will make it look like you’re just wearing a regular pair of dress shoes. 

Promising Review: 

I bought Clarks for the support, and as a teacher who is constantly on his feet,

I appreciate the support and comfort that Clarks is known for providing! 

– woodin

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Essential Details Waterproof Wingtip

Rockport Men’s Essential Details Waterproof Wingtip Oxford Shoe
  • 4.5 Stars
    • 640 Ratings 

The perfect blend of waling shoes and dress shoes, Rockport’s Essential Details wingtip is designed to stand up to the elements. 

Combining a classic brogued leather upper with a cushioned footbed made from the same adiPRENE tech that Adidas uses, it conform to your feet to provide a strong level of comfort. 

Plus, it uses HydroShield waterproofing to keep the elements out and your feet feeling dry, making these as good for pounding the pavement on the way to work as they are on unforgiving concrete floors. 

Promising Review: 

These shoes are unbelievable. I’m thinking of buying two more pairs in case Rockport goes out of business. 

They look like normal dress shoes and very professional BUUUUUT they feel like tennis shoes. Mega comfortable and gets compliments routinely at work.  

– JonnyMiami

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GH Bass & Co 


  • 5 Stars
    • 4 Ratings 

For those who prefer comfortable slip-on dress shoes, GH Bass & Co’s Larson combines the classic desing of a penny loafer with a cushioned footbed that’s (almost) worthy of New Balance.  

They have a chunky and thick sole that provides a lot of comfort, but also gives the shoes a hearty, kick-ass-and-take-names vibe.

And they’re further distinguished by the reddish hue of the wine color, which is more distinct (and in my opinion, more dapper) than a standard brown dress shoe.

Promising Review: 

Awesome Loafer! I absolutely love these shoes. They fit great right out of the box. 

They look great and are super comfortable. Highly recommend. 

– Daniel

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Hush Puppies

Men’s Bennet Wingtip Oxford

Hush Puppies Men's Bennet Wingtip Oxford
  • 4.3 Stars
    • 20 Ratings 

Best known for their comfortable walking shoes, I’ll be the first to admit that Hush Puppies isn’t the first brand that comes to mind when you think of the best men’s dress shoes. 

But they’ve always been experts when it comes to providing a comfortable fit, and their full-grain leather Bennet oxfords provide the right look for stepping up your shoe game.

The flexible uppers are made with the company’s “PerfectFit Stretch System” that’s designed to hug your foot snugly, while the five-pod outsole provides more than enough comfort for all day wear. 

Promising Review: 

Super comfortable sporty meets professional shoe.

I was waiting for the Bennett’s to come out for months and they did not disappoint. 

My job consists of being on my feet constantly so I need a shoe that looked the part but also was comfortable.

– Matt93

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Cole Haan

Grand Ambition Postman Oxford

Cole Haan Grand Ambition Postman Oxford
  • 4.8 Stars
    • 9 Ratings 

Another stylish entry from Cole Haan, the Grand Ambition Postman model is about as sleek and stylish as dress shoes come, while still offering a ton of comfort and support. 

What’s cool about these ones is that they give the simplicity of the design gives the impression that the whole thing is made from a single piece of leather, making them look more like formal dress shoes than comfortable hybrids.

But make no mistake: with an EVA outsole and anatomically contoured footbed, the comfort is definitely there.

Promising Review: 

I am very pleased with these shoes for the look, fit and feel. They are so comfortable. 

– Keith K.

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Un Tailor Cap Toe

Clark’s Un Tailor Cap Toe
  • 4 Stars
    • 4 Ratings 

Quite possibly the most comfortable cap toe on the market, Clark’s Un Tailor model pairs perfectly with formal wear like a suit or tuxedo (when all the other guys are trying not to think about how much it hurts to wear monk straps). 

With a dual-density Ortholite footbed, high-rebound EVA sole and the type of heel that’s designed for shock absorption, they’ll keep you comfy without sacrificing any style points. 

Promising Review: 

My dad got this for me and i wear it to school, i’ve had it for almost 2 years and it still feels as comfortable as when he bought it. 

– RavC

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Men’s Sneaker Oxford

Ecco Men's Sneaker Oxford
  • 4.5 Stars
    • 43 Ratings 

Ecco’s one of the most trusted names in comfortable footwear for decades, so it’s no surprise that they also make one of the most comfortable dress shoes on the market.

What might be surprising, however, is just how damn dapper they look.

Available in either all black or the eye-catching oxblood color pictured above, they combine a shock-absorbing outsole with a refined and sophisticated toe shape, in addition to a handsome broguing pattern.

The result is a remarkably stylish dress shoe from a brand that’s more traditionally known for making the best work shoes for retail and other standing-intensive jobs.

Promising Review: 

They are beautiful so many compliments they are very comfortable and true to size. 

– Eli

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Casual Dress Shoes

Vostey Casual Dress Shoe
  • 4.4 Stars
    • 1,139 Ratings 

It’s certainly not the most unique look, since both the design and fit of the shoe look suspiciously like Cole Haans.

But these are nonetheless solid crossovers that will work both at the office with a nacy suit, and with jeans for happy hour at the end of the day.

Plus they’re available in a whopping 11 different color options, making it easy to find not only the right size, but the right style to suit the rest of your wardrobe.

Promising Review: 

I was a bit skeptical when I ordered these. I have worn traditional leather sole shoes for ten years and the wear and tear on my knees and back was just too much.

I work in finance and a friend recommended I look for something easier on the feet. I found these and have been very pleased. So much more comfortable than my other shoes. 


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Total Motion City

Rockport Total Motion City
  • 4.7 Stars
    • 29 Ratings 

Another solid option from Rockport, these ones are styled after a plain toe Derby, rather than a wingtip like the Essential Details model above.

In addition to a more streamlined look, they come in a wider variety of styles.

You can get a suede upper in two different colors (beige or the blue pictured here), a brown version with white outsole, or a sleek all-black option that makes it look like a more formal shoe.

Promising Review: 

Best shoe I’ve ever owned…

…Shoe looks gorgeous and perhaps even designer. The fit and comfort is what you know from Rockport which is the best. I could not have found a better shoe... 

W. Faulkner

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Bruno Marc

Oxford Dress Sneakers

Bruno Marc Comfortable Dress Shoes
  • 4.4 Stars
    • 2,570 Ratings 

This option from Bruno Marc combines a 100% premium leather upper with a lightweight and durable MD outsole that provides plenty of comfort.

It also happens to have a one-inch heel height, which short vertically challeneged guys like me certainly appreciate!

Promising Review: 

These shoes are just what I wanted. They are comfortable and light. I wanted a shoe that was different and these fit the bill.

They are casual but can be worn with slacks for a formal look. The price is a fantastic value. And let me add, they are well made. I would buy again in a flash.

Bud Brooks

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Oxford Dress Shoes

Arkbird Oxford Dress Shoes
  • 4.2 Stars
    • 631 Ratings 

This shoe from Arkbird leans a little more toward sneaker territory, but the wingtip/broguing pattern around the toe cap helps elevate it, making it perfect for pairing with a business casual get-up.

Promising Review: 

These shoes are wonderful. At this price point I wasn’t expecting much to be honest but they had so many positive reviews online that I decided to try them out.

From the attention to detail to the padding inside they are as good as shoes 2 to 3 times the cost.

– jbinchrist

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Bruno Marc

Plain Toe Derby Dress Sneaker

Bruno Marc Plain Toe Derby Dress Sneaker
  • 4.5 Stars
    • 55 Ratings 

This derby from Bruno Marc has a sleeker look than the wingtip Bruno shoe above thanks to a plain toe and a thinner sole that keeps it looking more sophisticated.

Promising Review: 

I love these shoes! Perfect fit, very comfortable and look so good; I’m very pleased.

– Jamieman

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Men’s Fashion Sneaker

Vostey Men's Fashion Sneaker
  • 4.4 Stars
    • 4,117 Ratings 

This sneaker from Vastey has just enough sleekness that it can pass a dress shoe, but there’s a slight caveat here:

The thick, flat shoe laces give it away as a sneaker.

Swap them out for a thin pair of dressier laces and these will all of a sudden look like a thick-soled pair of oxfords.

Promising Review: 

Comfortable fit and professional look. I wanted some classy yet comfortable shoes for business travel. These fit as expected and I wear size 10.

They are really comfortable so far and hold up well to walking around the city. I have received so many compliments.

– Sunshine Mel

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Nine West

Mens Wingtip Shoes

Nine West Mens Wingtip Shoes
  • 4.3 Stars
    • 325 Ratings 

With thick rubber soles and an eye-catching navy blue color, these handsome, hearty brogues from Nine West are to the modern man what wingtips were to the English hunting parties who first started wearing them:

The perfect shoe for trudging through the elements while still looking sharp as hell.

Promising Review: 

I bought these for my boyfriend to wear with his suits for his job where he is on his feet ALL DAY.

These are beautifully made and have all the class of a wingtip shoe, but with a sleek sneaker sole.

– K.Threatt

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Men’s Garett Plain Toe Oxford

Rockport Men's Garett Plain Toe Oxford
  • 4.6 Stars
    • 1,178 Ratings 

Yet another solid option from Rockport, this one might just be the sleekest of the bunch, particularly in the cognac color pictured here, which gives the leather a buttery soft, supple look.

Promising Review: 

I purchased these and a competitors brand in an old fashioned stand off. These won easily on comfort, looks AND price.

– Mark S.

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Brogue Formal Lace Up

Brogue formal lace-up
  • 4.4 Stars
    • 936 Ratings 

This sharp-looking pair from Jousen is available in six different colors and comes in either a brogued or plain-toe version, providing lots of options to suit just about any style.

Promising Review: 

These were an amazing value. They look great and feel great. I’m on my feet all day and they do not hurt my feet like my last shoes did.

– Onetime42

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More Resources ↓
More Men’s Shoe Advice:
More Insight on How to Look Good & Live Well:

The Recap ↓

Overall Best Dress Shoes That Feel Like Sneakers

Dave Bowden

Wolf & Shepherd Crossover™ Longwing


The Crossover Longwing model is damn near the perfect pair of shoes. From the top these look like sharp and stylish dress shoes (I love the toe design and simplicity of the leather), but the cushioned insole down below means you can go all day without worrying about any discomfort.


About Dave Bowden

Dave Bowden

Irreverent Gent founder Dave Bowden is a style blogger whose advice on how to look good and live well has been featured in some of the world’s most trusted publications, including New York Magazine, The Wall Street Journal, Business Insider and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and son, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well. (Don't worry—it's less creepy than it sounds!)