13 Stylish & Comfortable Dress Shoes That Feel Like Sneakers

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Around here we like to say that shoes are the secret weapon of style, but it’s not hard to understand why guys would want to find a pair that combines the style of dress shoes with the comfort of sneakers.  

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

Rubber sole dress shoes from Amberjack
Brands have (finally!) gotten wise, and are starting to offer dress shoes that combine style and comfort in equal measure
[image: Amberjack]

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.

Some 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 shock absorbers and comfort of sneakers.  

To help you find a pair that will keep you looking well appointed and feeling well supported, below I’ve rounded up a wide range of dress shoes that feel like sneakers. 

And just for (lame pun alert!) kicks (you were warned), I’ve even thrown in a couple pairs of sneakers that look like dress shoes.  


In a Hurry? Here’s the Gist ↓

The shoes that lean more toward style tend to sacrifice some comfort, while the most comfortable ones tend to have a more casual look that makes them hard to pull off at formal occasions and business meetings. 

Overall, the best option that manages to strike the right balance is from Amberjack. Cole Haan makes one in a more classic style that isn’t quite as comfortable, while Wolf & Shepherd’s version is comfy as hell, but has a stacked heel that makes it look less formal. 


Who Wrote This Article:

Irreverent Gent Founder and Editor-in-Chief Dave Bowden has been a service journalist for more than a decade, and his fashion advice and shopping recommendations have been featured in The Wall Street Journal, New York Magazine, and Men’s Health, among many others.

How We Created This List:

Style / Visual
Appeal

Comfort
& Support

In-Person &
Online Reviews

The two main criteria Dave used to assess each shoe were style and (obviously) comfort. 

In the style department, he considered the toe shape, material, construction, number of color options and overall appearance. 

For comfort, he examined the materials and level of support offered by the insole and midsole, and the grip/traction of the outsole. 

In addition, Dave was able to personally test a number of shoes himself to see how they perform in the real world. For those he couldn’t try in-person, he did a deep dive into user reviews to find out what other guys really think of each pair. 

To learn more about how we rate and review products, check out our product review and round up policy here

OK, enough jibber jabber! Let’s get to the shoes.


Look Sharp, Stroll Soft:

The Best Men’s Dress Shoes That Feel Like Sneakers


Overall Best Dress Shoe That Feels Like a Sneaker ↓

Amberjack Originals 

Amberjack Originals
Specs:
  • Personally Tested? Yes
  • Dress Shoe Type: Derby
  • Material of Upper: Full grain leather or Italian suede
  • Colors Available: 7 leather, 6 suede 
  • How It’s Sneaker-Like: Heat-activated insole, dual-density TPU outsole
Why We Like It: 

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 dress shoes you can wear damn near anywhere.  

Why Some Might Not: 

My only real complaint about these is the toe shape, which isn’t quite as svelte as the equally comfortable Wolf & Shepherd shoe below. 

It’s by no means a deal breaker (at least, not for me), and the slim profile of the heel still makes these a dressy and sophisticated choice.

But those who want a sharp toe and a low heel might have to sacrifice a bit of comfort and check out the formal options listed below.

Check Price ➤


Runner Up ↓ 

Wolf & Shepherd Longwing

Wolf and Shepherd Longwings
Specs:
  • Personally Tested? Yes
  • Dress Shoe Type: Oxford
  • Material of Upper: Full-grain Italian calfskin leather or suede
  • Colors Available: 3 leather, 4 suede
  • How It’s Sneaker-Like: Removable memory foam footbed, High-density TPU sole, High-traction, thermal rubber outsole
Why We Like It: 

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

(Side Note: They actually did a publicity stunt where they had marathon runner Juris Silenieks wear their dress shoes to run a half-marathon in Atlanta… and the sonofabitch won.) 

Their Crossover Longwing model is arguably their flagship shoe, 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. 

Why Some Might Not: 

While I love the toe shape and suppleness of the leather, the stacked heel gives them a unique look that leans more sporty than sophisticated, which is why these are in the runner up position. 

In some ways they’re sleeker and more comfortable shoes than the Amberjacks above, and probably the better choice if you spend long hours on concrete floors. 

But they have the type of heel that you’d expect to find on pairs of shoes from brands like Nike or New Balance, which makes them less versatile and harder to pull off with formal wear. 

At the end of the day, if you could somehow combine the low profile sole of the Amberjacks with the high quality upper of these Longwings, you just might have the perfect pair of shoes. 

But alas, for now you’ll have to choose which one is more suitable to your look and your life.  

Check Price ➤


Best Formal Dress Shoe with the Comfort of a Sneaker ↓

Cole Haan Men’s Modern Classics Cap Toe Oxford

Cole Haan dress shoes
Specs:
  • Personally Tested? No
  • Dress Shoe Type: Oxford
  • Material of Upper: Full-grain leather
  • Colors Available: 3
  • How It’s Sneaker-Like: EVA footbed, rubber pods at forefoot and heel of leather sole
Why We Like It: 

Cole Haan has been making comfortable men’s dress shoes for a long time now, so it’s probably not a big surprise to see them turn up near the top of the list.

What might be more surprising is the fact that we’ve opted not to include their ØriginalGrand wingtip oxford, which is one of the better known sneaker-dress-shoe hybrids on the market today. 

(We felt that the premium leathers and comfortable fit of both the Amberjacks and the Wolf & Shepherd Longwings above out-paced it for the title of best overall, though it probably would have been the second runner-up in that category.) 

While the ØriginalGrands couldn’t quite crack our top two in the best overall category, these Modern Classics are an excellent choice for guys who need formal dress shoes that don’t skimp on style, but still provide a comfortable fit. 

They have all the characteristics of a sleek formal shoe, including a svelte toe shape, low-profile heel height and supple leather, giving them the right look to pair with a black or navy suit for formal events. 

But they’re also leather-lined and come with an EVA footbed, so even though they don’t have the thick sole of the ØriginalGrand, they’ll still be pretty comfortable for long days at the office. 

Why Some Might Not: 

These ones are only available in three colors, two of which are black (there’s a regular black and a patent leather option), which kind of limits the variety of styles you can wear them with.

They’re also only available in a standard medium width, so guys with wide feet might want to look elsewhere.  

Check Price ➤


Runner Up ↓ 

Hush Puppies Men’s Cairo Oxford

Hush Puppies
Specs:
  • Personally Tested? No
  • Dress Shoe Type: Oxford
  • Material of Upper: Leather
  • Colors Available: 2
  • How It’s Sneaker-Like: “Bounce” footbed provides shock absorption  
Why We Like It: 

As a brand, Hush Puppies are fairly well known for making comfortable and high quality shoes, but not the first (or second, or third) name that comes to mind when you want formal dress shoes. 

While their Cairo Oxford doesn’t have quite the same sleek look as the Cole Haan Modern Classic above, it provides even more comfort while still being easy to pair with a suit. 

If you wear suits or formal clothes to work and need a good, comfortable pair of walking shoes for every day wear, then these should make great work shoes. 

Why Some Might Not: 

With these ones the sole is black on both the black and brown dress shoe models. 

For the black shoes that’s not a problem, as the rubber sole isn’t that thick and blends in well with the rubber leather. 

But on the brown version it makes the sole look a little chunky. It’s still not nearly as pronounced as the high heels on the Wolf & Shepherd Longwing above, but in my opinion it detracts a couple style points. 

Check Price ➤


Best Budget Option ↓

Marc Nolan Jasper Wingtip Sneakers

Marc Nolan Wingtips
Specs:
  • Personally Tested? Yes
  • Dress Shoe Type: Derby wingtip
  • Material of Upper: Full-grain leather
  • Colors Available: 3
  • How It’s Sneaker-Like: Insole padded with latex memory foam, shock-absorbing rubber soles
Why We Like It: 

I wasn’t expecting much from Marc Nolan’s wingtip/sneaker hybrids, and with good reason: 

At less than $150, they’re way cheaper than most of the top-tier brands in this space. 

But after months of fairly regular wear, they’ve proven to be a very pleasant surprise.

The leather isn’t as rich or supple as what you’ll get from any of the brands listed above, which is probably where the savings come from. 

But they’re quite a bit nicer looking than most shoes in the sub-150 price range, and the comfort, support and fit of the shoe were actually quite impressive. 

I probably wouldn’t wear these to a wedding, but if you’re looking to step up your shoe game in a business-casual office (or at happy hour after work), these are a solid, affordable option. 

Why Some Might Not: 

I went with the Burgundy color, which in hindsight was a mistake. 

Rich colors like Burgundy look sophisticated as hell when done right, but with a cheaper grade of leather they tend to look a little more “grape” than “wine,” which kind of detracts from the sophistication. 

Of the three different colors on offer – there’s also a black and a “cognac” option – Burgundy was probably the dumbest one to choose. 

Overall I’m still quite happy with the quality, but if I could do it again I’d opt for the cognac option. 

Check Price ➤


Runner Up ↓ 

Bruno Marc Casual Dress Shoes

Bruno Marc Casual Dress Shoes
Specs:
  • Personally Tested? No
  • Dress Shoe Type: Derby
  • Material of Upper: Polyurethane
  • Colors Available: Polyurethane
  • How It’s Sneaker-Like: PU memory foam cushioned footbed, flexible TPR sole with rubber outer
Why We Like It: 

File these under “cheap and cheerful.” 

While the Marc Nolan shoes above punch above their weight for shoes in the sub-150 price range, these all-synthetic shoes from Bruno Marc are even cheaper, costing less than 50 bucks. 

For that price you have to manage your expectations accordingly, and the PU upper obviously isn’t going to look as good as genuine leather, even a lower-grade leather like the kind used by Marc Nolan. 

But the PU footbed provides plenty of comfort, and while Bruno Marc offers a number of dress shoe/sneaker hybrids in a number of different styles, the low-profile sole actually makes these look a little sleeker than many of the other options. 

Why Some Might Not: 

As mentioned, these have a synthetic PU upper, which for some guys is a complete non-starter. 

If you’re cash-strapped and need something in the sub-50 dollar range this is about as good as it gets, but if you’re able to spend a little more I would definitely consider upgrading to the Marc Nolan model above. 

Check Price ➤


Best Tuxedo Shoe That Feels Like a Sneaker ↓

Allen Edmonds Park Avenue Dress Sneaker 

Specs:
  • Personally Tested? No
  • Dress Shoe Type: Oxford
  • Material of Upper: Patent leather
  • Colors Available: Just one (black) 
  • How It’s Sneaker-Like: “FlyForm” insoles, rubber cup soles 
Why We Like It: 

Depending on your perspective, these are either the most formal and stylish sneakers ever created, or the most comfortable pair of formal tuxedo shoes ever created. 

Either way, they’re easily the best dress shoe/sneaker amalgam to wear with a tux. 

In addition to a patent leather upper that makes them both appropriate and sharp for black tie events, they have the same (perfect) toe shape as Allen Edmonds flagship Park Avenue oxford. 

But down below, they have the rubber cup soles that Allen Edmonds uses for their sneakers, while the inside boasts the company’s shock-absorbing “FlyForm” insole.    

Why Some Might Not: 

Allen Edmonds categorizes these as a sneaker, rather than a dress shoe that feels like a sneaker, which may deter some people. 

In my opinion the toe shape, patent leather and overall appearance clearly make this a dress shoe in all but name, but guys who are going full black tie for their wedding might feel weird about wearing a sneaker. 

Check Price ➤


Runner Up ↓ 

Amberjack Tuxedo Shoe 

Amberjack Tuxedo shoe
Specs:
  • Personally Tested? No
  • Dress Shoe Type: Derby
  • Material of Upper: Italian patent leather
  • Colors Available: 2
  • How It’s Sneaker-Like: Heat-activated insole, dual-density TPU outsole
Why We Like It: 

Amberjack’s tuxedo shoes offer pretty much all the same advantages as the Originals listed above, but come in (a handsome-as-hell) patent leather that makes them perfect for black-tie events like weddings. 

Why Some Might Not: 

While they have all the comfort features of the Originals, they also have the same toe shape, which is not quite as sharp as you might like from a formal pair of patent leather shoes. 

In my opinion the presence of the patent leather actually helps mitigate the more casual vibes given off by the slightly rounded toe, since patent leather is inherently considered more formal and “fancier.” 

But some guys might prefer a sharper toe for tuxedo shoes, in which case the Allen Edmonds pair above may be the better bet.  

Check Price ➤


Best Casual Dress Shoe That Feels Like a Sneaker ↓

Nisolo Lightweight Flex Derby

Nisolo flex derby
Specs:
  • Personally Tested? No
  • Dress Shoe Type: Derby
  • Material of Upper: Leather
  • Colors Available: 2
  • How It’s Sneaker-Like: Shock-absorbing, cushioned insoles, 3x lighter than average derby
Why We Like It: 

The phrase “casual dress shoe” is kind of an oxymoron, but generally speaking, it refers to shoes that have a rounder toe shape and come in materials and colors that are easier to dress down and wear with jeans

And Nisolo’s “flex” derby is not only one of the best-looking shoes in that department, but boasts some innovative designs that make it one of the most comfortable. 

In addition to flexible uppers that are super lightweight and can be packed flat for travel, they come with shock-absorbing insoles that make them feel as light (or lighter) than sneakers, but look good enough to pair with everything from shorts and a tee to a full (if unlined) suit and tie.  

Why Some Might Not: 

They’re only available in two colors, one gray and one light brown they call “tobacco.” 

The other knock against them is the fact that shoes this lightweight really need to be warn in the right places (and right climates). 

This would be a great pair of spring or summer shoes, but if you live in a cold climate you’ll probably want to keep them in your closet come winter.

Check Price ➤


Runner Up ↓ 

Johnston & Murphy Jenson Longwing

Johnston & Murphy longwing
Specs:
  • Personally Tested? No
  • Dress Shoe Type: Derby wingtip
  • Material of Upper: Italian calfskin leather or suede
  • Colors Available: 2 leather, 1 suede
  • How It’s Sneaker-Like: “Extralight” EVA sole, cushioned leather-covered footbed
Why We Like It: 

J&M’s Jenson wingtips are significantly heartier than the light weight Nisolos listed above, making them a great alternative to Chelsea boots and other casual dress boots. 

They’re available in a couple different colors, but my favorite is the one with an Italian suede upper in taupe, which strikes the perfect balance between casual and sophisticated. 

Why Some Might Not: 

The white sole on these is fairly thick and sneaker-like, which might deter some people.

The svelte toe shape and handsome broguing go a long way to keep the sophistication level high, but if you’re looking for sneaker-like comfort without the faintest hint of a sneaker-like appearance, you might be turned off.  

Check Price ➤


Best Slip-On Dress Shoes that Feel Like Sneakers ↓

Amberjack Loafer

Amberjack Loafer
Specs:
  • Personally Tested? Yes
  • Dress Shoe Type: Loafer
  • Material of Upper: Full grain leather or Italian suede
  • Colors Available: 6 leather, 5 suede
  • How It’s Sneaker-Like: Heat-activated insole, dual-density TPU outsole
Why We Like It: 

This is now the third pair of Amberjacks to crack this list, which should give you some sense of what a big fan I am. 

I own a pair of the Amberjack Originals, Loafers and Chelseas, and have been mighty impressed by the way they’ve merged comfort and style. 

This one has the same heat-activated insole as the Original and the Tux shoe listed above, but comes in a loafer style that’s classic, versatile and sophisticated, despite the ample comfort down below. 

I’ve got the brown suede color they call “Grizzly,” which is kind of like a tan or cognac color, and goes well with light and medium shades of blue. 

But I’m tempted to pick up the dark-brown “Chestnut” leather pair as well, which have a more formal vibe and would work better with darker shades like navy. 

Why Some Might Not: 

When it comes to loafers, some guys prefer penny loafers because they assume that the additional leather strap on the vamp (aka the top of the shoe) looks a little more sophisticated than having just a plain, single piece of leather. 

Personally I like both looks, but if you’re a penny-or-bust kind of guy, the model below might be more to your tastes.  

Check Price ➤


Runner Up ↓ 

Wolf & Shepherd Crossover Loafer

Wolf and Shepherd Loafers
Specs:
  • Personally Tested? Yes
  • Dress Shoe Type: Penny Loafer
  • Material of Upper: Full-grain Italian calfskin leather or suede
  • Colors Available: 3 leather, 4 suede
  • How It’s Sneaker-Like: Removable memory foam footbed, High-density TPU sole, High-traction, thermal rubber outsole
Why We Like It: 

And speaking of penny loafers, these are easily the most comfortable pair on the market. 

Wolf & Shepherd’s Crossover Penny was one of the (many) models I tried to conduct my full Wolf & Shepherd review, and I was pretty impressed.   

Whether or not a penny loafer counts as a dress shoe really comes down to the shape of the toe box, and like most of Wolf’s other dress shoe hybrids, these have a damn-near-perfect toe shape that’s sharp and sophisticated. 

Plus the leather is soft and supple, which make them comfortable enough to wear without socks, which is a plus because I personally prefer the sockless look while rocking loafers.   

Why Some Might Not: 

Like Wolf & Shepherd’s other crossover shoes, these ones again have a thick rubber sole that makes them scream “hybrid” rather than “pure dress shoe.” 

I’ve included two Wolf shoes on this list so obviously the thick sole doesn’t bother me too much, but I know some guys don’t like it.  

Check Price ➤


Best Sneakers that Look Like Dress Shoes ↓

Allen Edmonds Strand Oxford Dress Sneaker

Allen Edmonds Strand Dress Sneaker
Specs:
  • Personally Tested? No
  • Dress Shoe Type: Oxford
  • Material of Upper: Calfskin leather or suede
  • Colors Available: 2 leather, 5 suede
  • How It’s Sneaker-Like: “FlyForm” insoles, rubber cup soles
Why We Like It: 

Much like the Allen Edmonds Park Avenue sneaker above, the Strand is technically a sneaker, but it looks so damn much like a dress shoe that it seems crazy not to include it here. 

It has the classy and timeless toe shape that AE’s regular dress shoes are known for and uses the same FlyForm insoles as the Park Avenues to provide sneaker-level comfort. 

Oh, a quick note about AE’s website: 

There are seven different colors available, but the way they list their products is kind of weird, so unfortunately I can’t give you a link to a single product page from which you can choose your preferred color. 

The link above sends you to one version, the Chestnut brown leather pair, but if you use the search bar at the top of that page to enter the words “Strand dress sneaker” you’ll get a search results page that shows you all the available colors. 

Sorry for the hassle! 

Why Some Might Not: 

Unlike some of AE’s other dress sneakers, these ones have a broguing pattern. 

Personally I think the broguing adds a rugged touch that nicely juxtaposes the sneaker sole, but I know brogues aren’t for everybody. 

Check Price ➤


Runner Up ↓ 

Johnston & Murphy McGuffey Lug Plain Toe Sneakers 

Johnston and Murphy sneaker
Specs:
  • Personally Tested? No
  • Dress Shoe Type: Derby(ish)
  • Material of Upper: Full-grain leather
  • Colors Available: 2
  • How It’s Sneaker-Like: “Trufoam” footbed, lug rubber sole 
Why We Like It: 

This shoe goes in pretty much the exact opposite direction of the Allen Edmonds one above. 

Johnston & Murphy’s McGuffey falls quite squarely in the “sneaker” category, but has the lug sole and outer stitching made famous by brands like Dr. Martens. 

The result is a sneaker that looks enough like a (casual) dress shoe that it could work well in a casual office, and pair well with jeans, khakis or shorts. 

Why Some Might Not: 

As mentioned, this one is much more casual—the toe box is quite rounded and the lug sole is rugged, but not particularly refined. 

So it’s not the best option if you’re looking for a pair you can wear with suits or other formal clothes. 

Check Price ➤


More Resources ↓
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Banner Photo: Cole Haan
Banner Illustration: Irreverent Gent

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, 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!), or email him at [email protected] if you want to get in touch.

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