The Best Dress Sneakers for All-Day Comfort

While dress shoes are a clearly defined category, dress sneakers are not. In fact, the phenomenon is still in its relative infancy, even if men have been wearing sneakers with suits, dress pants and other dressier clothes for more than a decade now. Oftentimes, they look stylish. Other times, they do not. Here’s how to look good doing it.

Dress Sneakers History

Early on, it was just Chuck Taylors. In 1983, Irwin Corey wore low-top Chucks on David Letterman. A decade later, Ellen Degeneres wore a number of sneaker-and-suit sets on her show, The Ellen Show. Sure, these folks aren’t traditional style icons, but they set the trend in motion, even if it always existed in some subsets.

By the early 2000s, sneakers were slowly becoming more acceptable in more places. When Common Projects introduced its all-white low-top leather sneakers in 2004, they spread like wildfire, triggering tons of copycats. Now, the style may be the most ubiquitous sneaker of all time — the blankest, but also boldest, fashion statement you can make.

What made them so popular, though, was the low-top leather sneaker’s ability to blend into any wardrobe, whether you dressed up every day or simply wore sweatpants. Then, Adidas reissued the iconic Stan Smith, a sneaker they had shelved until 2014. These are admittedly more informal than the Common Projects, but they pushed plain sneakers further into the fold.

From there on, most menswear magazines featured some form of the sneakers-with-formal-clothes outfit, a reaction to the growing demand for designs that serve more than one purpose (i.e. sneakers you can wear with dress pants and sweatpants).

What Are Dress Sneakers?

So, what exactly are dress sneakers then? Do brands specifically call them that? Well, no — it’s more of a feeling, than a true checklist. In general, dress sneakers are flat-soled sneaker and almost always made from leather or suede — hence why you’ll see several sleek sneakers with white soles and suede uppers. It’s best to avoid sneakers with pronounced or ridged outsoles — they look more fitness-focused, not formal — or mesh or fabric accents.

Can You Wear a Suit with Dress Sneakers?

As proved above, of course — just do it sensibly. While you may see some of your favorite celebrities strolling red carpets in expressive suit-sneaker combos, these sartorial cocktails are best saved for folks with teams dedicated to making sure things fit, look and feel right.

That’s not to say you aren’t capable of dressing yourself, but Dior Jordan 1s are never a good look with a J.Crew suit, if you get what I’m saying. Don’t simply put two things together because you like both of those things. Be more intentional about it. Think about how they look and feel together and whether they tell a unique story.

Chucks and a tailored tuxedo are always a look, even if there are more comfortable sneakers out there. A modern, performance-focused suit with all-leather sneakers is another solid look, and they’ll look just as good when you inevitably ditch the jacket, too.

Koio Capri

KOIO

Best Overall Dress Sneaker

Koio Capri

• $295.00 at KOIO

• Material: Leather
• Color(s): 28
• Size(s): 7-13

Koio’s Capri is the quintessential low-top leather sneaker. It’s essentially logo-less, with debossed text only at the heel. Otherwise, these are all white (or whatever color you choose). Each one is made with smooth Vitello calf leather, with a removable insole, a lightweight Margom outsole and a calf-leather lining.

They’re comfortable, too, from the first wear but only get better with time. And they’re easy to clean, too, our tester found. A wet rag removes most stains, while a dedicated sneaker cleaner can tackle the rest. Sure, the $295 price tag is high, but these will last a lot longer than a pair of Vans, for example.

Loro Piana Ultimate Penny Loafer

Nordstrom

Best Upgrade Dress Sneaker

Loro Piana Ultimate Penny Loafer

• $1,075.00 at Nordstrom

• Material: Suede
• Color(s): 3
• Size(s): 40-46 (EU)

A staple in the ultra-luxury scene, Loro Piana doesn’t just provide materials to other brands. It also makes its own in-house goods and has since the ’80s. (That’s not news to any fans of the brand, obviously.) Among its core products are its comfortable dress shoes, which range from the mid-height Open Walk Chukka Boots to these, the Ultimate Penny Loafer.

They’re made from soft, Loro Piana suede with a leather liner and a grippy rubber sole. Are these true loafers? No, but you can wear these without losing your silhouette. Plus, they’re Loro Piana. These cost way more than most dress shoes.

Beckett Simonon Reid Sneakers

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Best Affordable Dress Sneakers

Beckett Simonon Reid Sneakers

• $169.00 at beckettsimonon.com

• Material: Leather
• Color(s): 6
• Size(s): 7-14

Similar to Koio’s shoe but not quite the same, Beckett Simonon’s sleek Reid Sneakers are actually logo-less: no debossed text logos, no tags. These are simple, well-made sneakers with full-grain calfskin leather uppers. They’re waxed, too, for durability, but also so that they break in more softly over time.

Most reviewers find them comfy straight from the box, but some cite rubbing at the heel, which can happen if you don’t wear long socks. It can happen, too, if your socks are too thin. That’s actually the case with most dress sneakers: dress socks don’t work particularly well unless you tie your shoes pretty tight.

SuitSupply Suede Slip-On

Suit Supply

Best Loro Piana Alternative

SuitSupply Suede Slip-On

• $499.00 at Suit Supply

• Material: Suede
• Color(s): 3
• Size(s): 6-13

SuitSupply didn’t drop these to directly compete with Loro Piana’s line of soft-soled dress sneakers/shoes, but they’re clearly inspired by them. Or, perhaps the broader category at large, which is ever-expanding and now includes a number of loafer-inspired designs.

SuitSupply’s, however, are made from Italian calf suede uppers and a calf leather liner, with natural rubber soles cemented on. That makes these lightweight and comfortable, but not resoleable, of course, like some loafers. They’re much lower profile, too, with their shorter upper and thinner outsole, but that makes them great for a sort-of-skinny suit or a summer-y matching set.

Allen Edmonds Park Avenue Oxford Dress Sneaker

Park Avenue

Allen Edmonds Park Avenue Oxford Dress Sneaker

• $295.00 at allenedmonds.com

• Material: Leather
• Color(s): 3
• Size(s): 6.5-15

A riff on the brand’s popular Park Avenue Oxford dress shoe, which was introduced in 1982, Allen Edmonds’s Park Avenue Oxford Dress Sneaker is the same shoe with a new outsole: white rubber instead of stacked leather. That means these look like Oxfords but act, feel and function like sneakers.

That’s a strange combo for some folks, but others aren’t quite ready to make the jump from decorated dress shoes to simpler, plainer sneakers. Hence why these exist. Are they cooler than the lug version? No, but they’re more comfortable, and they, too, can be recrafted by the experts at Allen Edmonds.

Cole Haan OriginalGrand Wingtip Oxford

Cole Haan

Best Dress Shoe in Disguise

Cole Haan ØriginalGrand Wingtip Oxford

• $150.00 at Cole Haan

• Material:
• Color(s):
• Size(s):

Cole Haan’s category-defying OriginalGrand Wingtip Oxfords set the comfortable dress shoe craze in motion when they debuted with Nike when Nike owned Cole Haan. Then, the outsole was Lunarlon foam, a ridge foam-filled material that offered better bounce and enhanced cushioning.

Once Nike sold Cole Haan, the brand was forced to make its own outsole, which they now call ZeroGrand. The OriginalGrand iteration, however, references the earlier collaborative design. It has the same ridges and bends and bounces the same, even if it isn’t from Nike.

These are therefore quite the statement, but plenty of folks love them because they’re comfortable and they can pass for standard Oxfords from far enough (or in photos).

Wolf and Shepherd Crossover Loafer

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Best Dress Sneaker for Long Days

Wolf and Shepherd Crossover Loafer

• $279.00 at wolfandshepherd.com

• Material: Leather
• Color(s): 5
• Size(s): 6-15

A true hybrid if there even is such a thing, Wolf and Shepherd’s Crossover Loafer looks like a crossover — like the car. It has a sneaker chassis and a standard loafer upper and makes no real attempt to be too much like either influence. It’s firmly down the middle, with its memory foam footbed, high-density outsole and water-resistant scuba liner.

If you work long days on your feet but still need to be (semi) dressed up, these are a smart choice.

Common Projects Achilles Sneaker

MR PORTER

Best Trend-Setting Dress Sneaker

Common Projects Achilles Sneakers

• $410.00 at MR PORTER

• Material: Leather
• Color(s): 8
• Size(s): 37-47 (EU)

The sneaker that started it all: Common Projects’ Achilles Sneaker. Introduced in 2004, the pared-back design struck a chord, quickly becoming the go-to grail for everyone over the age of 18. They worked with jeans, trousers, shorts and seemingly everything in between — including suits.

But with its $400+ price tag, plenty sought out cheaper options, triggering an avalanche of white and off-white, all-leather sneakers. Now, there are dozens of options to choose from, but Common Projects are now the classics, even though they’re less than 20 years old. If you want an all-white leather sneaker, go straight to the source (and splurge, if you can).

Amberjack The Original

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Most Innovative Dress Sneaker

Amberjack The Original

• $179.00 at amberjack.shop

• Material: Suede
• Color(s): 9
• Size(s): 7-13

Truthfully, I’m new to Amberjack’s shoes. That being said, I’m impressed. I actually saw a pair on someone else first, not online, and I was surprised by how much they looked like a standard suede Oxford. How convincing they really are changes from pair to pair — the tonal slate iteration is the most deceptive, I’d say — but the pairs with matching outsoles would pass for standard dress shoes 9 times out of 10.

Flip them over, though, and you’ll find an outsole fit for a running shoe. There’s a flat stretch of tread at the forefoot (the balls of your feet), but the rear is split like a fin, lending pep to your step. Within, there are even more comfort-focused elements. The insole, for example, is heat-activated, which means it’ll mold to your feet faster, and stay molded for for longer.

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