9 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.  

In this post I’ve rounded up more than a dozen different styles of comfortable dress shoes that feel like sneakers, each of which will keep you both well appointed and well supported.

The Best Dress Shoes That Feel Like Sneakers

Breaking Down the Most Comfortable Dress Shoes for Men

Wolf & Shepherd 

Crossover™ Longwing

Wolf & Shepherd Crossover™ Longwing
  • 5 Stars  
    • 421 Ratings 

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 worry 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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Clark’s 

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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Wolf & Shepherd 

Crossover™ Wingtip 

Wolf & Shepherd Crossover™ Wingtip
  • 5 Stars  
    • 63 Ratings 

Another entry from Wolf & Shepherd, the wingtips combine the same comfortable tech that makes the Longwings above such a stand out with the classic style of brogues. 

Wingtips are generally considered a slightly more casual look than other types of dress shoes, which lends itself well to the cross-over sneaker model and its padded soles. 

As with the Longwings, the toe shape is on-point here and the leather is high-quality, making these a great alternative for those who prefer the wing-tipped look.

Plus, Wolf & Shepherd donates a portion of sales to the Steve Nash Foundation, which helps make underserved children healthier and happier.  

Promising Review: 

Beautiful shoe and super comfortable. You can wear them with anything from jeans to a suit. I ordered a 1/2 size up, perfect fit. 

– Jim

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Johnston & Murphy 

XC4® Elkins Wingtip

Johnston & Murphy XC4® Elkins Wingtip
  • 4.5 Stars  
    • 126 Ratings 

J&M’s XC4 Elkins wintip has all the style of a sophisticated pair of brogues and all the comfort that their XC4 line has become known for. 

The padded sole provides support in all the right places while the sleekness of the design makes these great for formal occasions like weddings when you might be on your feet for a long time. 

Promising Review: 

I walk to work and use a standing desk so my shoes can take a beating. These are very comfortable and finally there is a dress shoe in the XC4 line. 

– Anthony F.

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Clark’s 

Chantry Wingtip

Clark’s Chantry Wingtip
  • 5 Stars  
    • 1 Rating

Clark’s brogued Chantry model is another pair that combines the masculine style of wingtips into stylish and comfortable shoes. 

Available in four different colors, it’s lined with sheepskin on the inside and comes with Clark’s Extralight EVA midsole, making it hard for even the best sneakers to compete with it when it comes to comfort. 

Promising Review: 

I bought this pair for work and I have received nothing but compliments. Great quality, feel and look. Highly recommended. 

– shelkesid

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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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Rockport 

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 

LARSON 90S WEEJUNS

GH Bass & Co LARSON 90S WEEJUNS
  • 5 Stars  
    • 1 Rating 

For those who prefer 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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Johnston & Murphy

XC FLEX™ Cody Longwing

Johnston & Murphy XC FLEX™ Cody Longwing
  • 4.5 Stars  
    • 25 Ratings 

Johnston & Murphy’s Cody Longwing is a good alternative to the Elkins model listed above, and is arguably even more handsome. 

The full-grain leather upper comes in a rich brown color, while contrast cross-stitching connects the comfortable rubber lug sole, resulting in a shoe that’s as easy on the eyes as it is on the feet. 

Promising Review: 

Love this shoe like no other. The most supportive/comfortable shoe I’ve ever worn and at a very fair price point. 

I own several styles and am considering their new golf shoes.

– James

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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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Clark’s 

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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Amberjack

The Original

Amberjack The Original
  • 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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About

Irreverent Gent founder Dave Bowden is a men’s style specialist, an Amazon bestselling author, an unrepentant introvert, a long-suffering (but very patient) Toronto sports fan and the husband of a wonderful (and thankfully even more patient) wife.