20 Of The Most Comfortable Shoes To Help You Get Through The Day (Updated 2022)


Comfort and style didn’t use to be mutually exclusive, but today the most comfortable shoes for men are also some of the most fashionable. From dressed-up styles to pure athletic wear, comfortable shoe options are far and wide (like some men’s feet). 

We’ve taken the time to narrow down the most comfortable shoes for men. Yes, and the most good-looking ones as well. Rather than Sketchers and orthopedics, this article focuses on sleek additions to any man’s footwear collection. Plus, an extra dose of comfort for those long days on your feet. 

If it’s time to upgrade your footwear game, keep reading to discover your next pair of go-to kicks.

 

man sitting on a chair with feet up
wear.amberjack / Instagram

When it comes to the most comfortable shoes for men, the CLAE Bradley sneakers reign supreme. The shining feature of these bad boys is the neoprene heel. It looks slick and creates a satisfying experience of slipping the shoe on and off. 

Neoprene also prevents leather from rubbing against your heel. Though that’s not much of an issue here, considering CLAE sneakers use a softer leather than other brands.

Then comes the foam insole and the water-resistant construction. These features make this shoe that much more practical for year-round wear, crowning it as the most comfortable and stylish shoe overall. Easy to dress up or down, pair these sneakers with jeans, slacks, or even basketball shorts—they work with it all.

Material: Leather | Sizes Available: US 4 – 14 | Colors Available: Brown, White, Black, Navy, + | Formality: Smart Casual

CLAE Bradley Essentials Sneaker

Amberjack is a big name in the world of the most comfortable men’s shoes, and with good reason. This Brooklyn-born brand puts a special emphasis on comfortable dress shoes for men that will carry you to the office and beyond.

They only have two collections, which allows them to stick to the perfect essentials. There is a twist, though. The Original dress shoes are made in Portugal from A-grade full grain leather, with soft lining and a foam insole. But instead of memory foam, Amberjack uses a special kind of foam that activates with heat and provides long-lasting arch support.

That means these stylish shoes are comfortable right out of the box. They’re the ideal accompaniment to any business casual getup. We’re thinking navy suits, crisp white Oxfords, and your favorite pair of colorful dress socks.

 Material: Leather | Sizes Available: US 7 – 13 | Colors Available: Chestnut, Honey, Onyx, Obsidian (Leather), + | Formality: Dressy

Amberjack The Originals

Dress shoes aren’t often thought of as comfortable. In fact, most dress shoes are wildly rigid and unforgiving. But not this pair of Oxfords from Myrqvist. This Swedish brand has pulled out all the stops to make shoes that are easy on the feet and sharp on the eyes. 

The high-quality construction is designed for anything from sitting at a desk to miles of commuting. Though if you do plan on walking long distances, consider the leather sole over the half rubber sole for longevity. 

As a bonus, these black calf leather Oxfords are easy to break in (yes, you can wear them to work straight out of the box). Of course, they look great with office attire, but you can also rock them with khakis or selvage denim and a tee. Whatever outfit you choose, they’ll keep looking great even after years of wear.

 Material: Leather | Sizes Available: US 5.5 – 13.5 | Colors Available: Black Calf, Black Patent Leather, Dark Brown Calf, Dark Brown Suede | Formality: Dressy

Myrqvist Äppelviken Black Calf Oxfords

This high-end sports shoe has a cult-like following thanks to the insanely comfortable fit. Reviewers dub the shoe as walking on clouds and compare them to wearing slippers.

The technical specs of this sneaker don’t leave you wanting for much. The cushioned sole is similar to bouncing on springs, and the mesh upper can accommodate standard and wide fits—no squished toes here. Fourteen stunning colorways don’t hurt either. Our pick is all black, which can be dressed up with a pair of jeans and a polo or kept for athletic wear with shorts or sweats. 

Material: Mesh | Sizes Available: US 7 – 15 | Colors available: 14 Colorways | Formality: Athletic

Saucony Triumph 19 Sneakers

These modern derby sneakers provide a much-needed respite from the world of austere work shoes. And they’re as comfortable as they are stylish. This hybrid suede shoe not only looks good but also molds to your feet for a customized fit. 

The sustainable, plush sole and hand-stitched details are just the start. They also come in eleven colors. It’s clear they’re a fundamental statement piece for a professional wardrobe. 

They look equally at home with business casual as they do with pub clothes. If you’re looking for versatility in the styling options, this is it. And for an extra dose of comfort, it’s worth noting that Crown Northampton accommodates wide feet. Simply request a ‘G Fitting’ in the checkout box when ordering. 

Material: Deer Suede | Sizes Available: UK 3 – 14 | Colors Available: 11 Colorways | Formality: Smart Casual

Crown Northampton Harlestone Hand Stitched Derby

Whether you’re working in a restaurant or a warehouse, the most comfortable men’s shoes for standing all day are a necessity. And these Asics fit the bill to a tee. These favorite fan shoes have no break-in period, so they’re ready to get you standing right out of the box.

The latest installment in the Gel Venture line, this model has gel embedded in the rubber sole to absorb shock. The deep lugs on the bottom of the shoe provide superior traction, and they come in wide and narrow fits. If you’re after something slightly flashier than plain black, these shoes also feature a whopping 26 colors to choose from.

Material: Synthetic | Sizes Available: US 7 – 15 | Colors Available: 26+ | Formality: Athletic

Asics Gel Venture 8 Sneakers

There’s no market quite as saturated as the athletic one. But once you break free of the big brand names, you’ll find the options are plentiful. Plus, an extra helping of style and a heaping serving of comfort. 

These running shoes from Hylo are among the most comfortable options out there. The proof is in the first-rate arch support and accommodation for narrow feet. And these low-profile sneakers are lightweight, cushioned, and designed for speed. Not to mention they’re completely recyclable and made by runners for high performance. 

Thanks to the parred back design, it’s simple to dress these runners up with a pair of slacks or jeans. For a more street-style inspired outfit, consider wearing them with a pair of cargo shorts and a flashy hoodie or graphic tee.

Material: Mesh | Sizes Available: US 7 – 14 | Colors available: Khaki, Black, Blacksand, Blackwhite, + | Formality: Athletic

Hylo Athletics Run 2

Wedding shoes can be a tricky business. You want something nice enough to suit the dress code but comfortable enough to wear without getting blisters. These derby-style dress shoes from Clarks are some of the most comfortable men’s shoes on the market. And they also make for stunning wedding footwear, whether you’re the groom, best man, or another name on the guest list. 

While it’s undeniable these are some good-looking leather shoes, the devil is truly in the details. The footbed has a highly cushioned dual density foam, and the upper is completely breathable for all-day wear. They’re a medium-width design to accommodate a wide range of feet and work for weddings of all dress codes. 

For a black tie event, they’ll mesh seamlessly with a tux. And for a warm weather wedding, match them with khakis or ironed slacks, with a white or light blue Oxford. 

Material: Leather | Sizes Available: US 7 – 13 | Colors Available: Dark Tan, Black, Light Grey (Nubuck), + | Formality: Smart Casual

Clarks Atticus Leather Shoes

Casual and comfort go hand in hand, and no brand does it quite like Axel Arigato. Fusing elements of simplicity and style, this brand doesn’t fail you with their casual shoe collection. 

With retro vibes for the modern man, this best-selling leather shoe is designed to wear beautifully for a timeless look. Yes, even after dragging them across the world and back. Handcrafted in Portugal, the Dice Lo sneakers are soft and comfortable enough for all-day wear. Ideal for heading out for the weekend or packing them for your next big trip. 

If you’re looking to replace your scuffed-up Stan Smiths, these are the ultimate upgrade. Wear them with jeans, shorts, or even sweatpants with a plain white tee… all eyes will be on your footwear anyways. 

Material: Leather | Sizes Available: US 7 – 13 | Colors Available: 6 Colorways | Formality: Casual

Axel Arigato Dice Lo Sneaker

It’s pretty insane to think about a dress shoe-sneaker hybrid, but Cole Haan went there. And it looks damn good. In theory, this concept makes perfect sense, and the execution is really well done. Featuring a leather wingtip Oxford upper and a sneaker-like sole, these are some of the most comfortable shoes for men of all time. And the most stylish, too.

Designed for maximum traction to handle any kind of terrain, the soles are extra cushioned to respond to each step you take. They’re a practical choice for frequent events on your feet. 

They also match just about anything, save for athletic wear. To dress them up, pair them with light-colored dress pants and a blazer. For a more casual look, jeans and a t-shirt is the definition of casual sleek.

Material: Leather | Sizes Available: US 7 – 16 | Colors Available: British Tan, Black, Tan-Java, Cobalt, + | Formality: Dressy 

Cole Haan Zerøgrand Wingtip Oxford

These iconic Chelsea boots are some of the best in the world. Namely because of how pleasant they are to wear—once they’re broken in, that is. From the streets of New York to Sydney, you’ll see these practical shoes everywhere. They’re rocked frequently by the likes of David Beckham, Brad Pitt, and Chris Pine.

These boots can withstand a lot because of their premium materials and top-notch shock absorption. Regardless of whether you’re a city slicker or country folk, they fit any and all scenarios. And they’re water resistant, too. Though the real value is in the footbeds (with a spare pair included), cushioned for extreme comfort.

Wear your Blundstones with cuffed jeans paired with anything from a premium cotton t-shirt to an ironed button-down or polo. You can even wear them with slacks to work. The neutral colorways of the boots create a classic look, no matter what you choose to wear them with.  

Material: Leather | Sizes Available: US 4 – 14 | Colors available: Black, Brown | Formality: Casual 

Blundstone Round Toe Chelsea Boots

It doesn’t matter what anyone has to say, duck boots are timeless, and L.L.Bean makes the best. When it comes to the winter footwear department (especially in the Northeast USA), these boots will keep your toes toasty and dry. Bonus points for also being the most comfortable pair you’ll ever own. 

L.L.Bean has combined two of their brand’s most comfortable products: Bean Boots and their signature flannel. Heck, why not line the boots with flannel? The flannel and the Thinsulate insulation lock in superior warmth on those snowy mornings. That said, if you don’t mind a bit of bulk, the heavier sherpa-lined Bean Boots are the way to go for optimal warmth. 

Though they’re perfect shoes for a snowy commute, Bean Boots complement any kind of look, from preppy to rugged. Wear them with polos, big winter jackets, tan pants or jeans. You’ll blend right in with the likes of Jake Gyllenhall and even Kanye, who has his own rendition of duck boots under the Yeezy shoe line. 

Material: Leather | Sizes Available: US 7 – 14 | Colors available: Classic Brown | Formality: Casual

L.L.Bean Flannel Lined Bean Boots 

Considering these shoes have been on the market since 1990, it’s unlikely they’re going anywhere soon. With more than 30 years under its belt, Nike Air Max 90s are some of the most comfortable men’s shoes that don’t skimp on style. This retro-inspired best seller has the namesake Max Air cushioning in the sole for top-notch performance comfort. Then it’s finished with a soft foam midsole, so every step is like walking on a cloud.

There’s nothing more classic than the design of this shoe. You can’t go wrong with multiple colorways to choose from and a soft upper that’s blister-free on your first wear. Pair them with jeans, khakis, and even shorts during warmer weather. These shoes are a choice accompaniment to a comfortable, casual look.  

Material: Textile & Leather | Sizes Available: US 6 – 15 | Colors available: Black, Black/White, Grey, White, + | Formality: Casual

Nike Air Max 90 Sneakers

The Driver loafers are the ideal slip-ons for summer, and they’re specifically designed with comfort in mind. Crafted from the softest Italian suede and finished with a microfoam footbed, these luxurious shoes are an excellent addition to any collection. 

Aside from the insane comfort, these shoes are worthwhile, thanks to Oliver Cabell‘s sound business model. Forget about the traditional retail markup. This brand works directly with consumers to deliver a high-quality product without price gouging. 

That makes it even harder to deny how good-looking these shoes are. They’re the ultimate choice for summer footwear without putting your toes on full display. Wear them with khaki shorts, collared shirts, and anything seersucker.

Material: Leather | Sizes Available: US 6 – 15 | Colors Available: 25+ | Formality: Smart Casual

Oliver Cabell Driver Loafers

While we’re not huge proponents of letting our toes roam free, sometimes sandals are necessary. So if you’re looking for the most comfortable pair for your next beach day or pool lounge, Birkenstocks take the cake. These days, this leather sandal is acceptable to wear without exuding Woodstock vibes. And hey, if Leo DiCaprio can wear them, you can too. 

The stellar design makes Birkenstocks a chart-topper, which has remained true since the early 70s. An ultra-supportive cork-latex footbed with a layer of foam and special molds for toes. It’s hard to find a sandal that accommodates feet quite like Birks do. Choose from a wide or narrow fit and a huge range of colors. And please, for the sake of fashion, don’t wear them with socks.

Material: Leather | Sizes Available: US 7 – 16 | Colors Available: 30+ | Formality: Casual

Birkenstock Arizona Sandals

Comfortable shoes are essential in the world of hiking, and these Solomon sneakers will take you from the street to the trail. Designed for soft, loose terrain, they’re a sturdy companion for any outdoor adventures.

These trail sneakers have a rare combination of superior traction and advanced stability. You can’t find that in typical shoes. The Speedcross sneakers cradle your heel and move seamlessly with your feet rather than working against you. 

Finished with an Ortholite insole for optimal cushioning with each step, you’ll be hard pressed to find a comfier option. And did we mention they’re secured with a drawstring, so there are no laces to tie?

Material: Textile | Sizes Available: US 7 – 14 | Colors Available: 6 Colorways | Formality: Athletic 

Salomon Speedcross 5 Trail Running Shoes 

Rigid leather high tops are a thing of the past. Welcome to the new age. The most comfortable men’s shoes are made from softer materials that sit gently against the ankles instead of incessantly rubbing with every single step.

Global brand Løci embodied the traditional high-top silhouette and gave it a twenty-first-century upgrade. Made from breathable vegan materials, these basketball shoes focus on comfort. Recycled ocean plastic, bamboo lining (no more stinky feet), and elastic cork insoles reduce stress on the joints. 

The ideal accompaniment to a sporty or retro outfit, these shoes serve serious Y2K vibes. They look great with old-school basketball shorts, cuffed jeans, and a graphic t-shirt or hoodie.

Material: Recycled Ocean Plastic | Sizes Available: US 4.5 – 13 | Colors available: 9 Colorways | Formality: Casual

LØCI Eleven High Top Sneakers

Do you have high arches or just need some extra support? These New Balance sneakers are among the most comfortable shoes for men out there. With more than 2500 positive reviews, these shoes are it if you suffer from any foot-related ailments.

Outfitted with an Ortholite insert footbed and excessive midsole cushioning, these sneakers are the ultimate dad shoes. Perfect for walking miles or standing all day. They also come in fits from extra narrow to extra, extra wide to match the sneaker exactly to your individual foot type. And the good news is, dad shoes are totally in now, so you’ll get extra style points from anyone who’s looking. 

Material: Suede & Mesh | Sizes Available: Us 7 – 16 | Colors Available: Grey, Black, Navy | Formality: Athletic/Casual

New Balance Made in USA 990v5 Core Sneakers

While these sneakers are the least stylish on our list, they’re certainly the most comfortable shoes for men on a budget. Well revered as walking on air, these leather Reeboks are loved for long days at work and walking great distances. 

The leather uppers make these shoes plenty water-resistant for wet days. And they have a low-profile black design to match with basic or bold closet staples. You’ll feel a real bounce in your step, thanks to the cushioned insole. These don’t leave you wanting for much when it comes to pure comfort.  

Material: Textile & Leather | Sizes Available: US 7 – 15 | Colors available: Black, White, White/Blue | Formality: Athletic

Reebok Walk Ultra 7 DMX MAX Sneakers

High-end Italian brand Loro Piana pulls out all the stops for their luxury footwear collection. Right off the bat, we’ll admit that nearly a grand is pretty steep for sneakers. But that’s the price to pay for some of the most comfortable shoes on the planet. This pair is comprised of knitted silk for next-level extravagance and forms around your feet for sock-like comfort. 

Best known for their cashmere knits, Loro Piana knows a thing or two about design. And this really shines through in the construction of this sneaker. Below the knit upper comes a cushy sole and fine leather detailing, which results in a lightweight shoe that’s well suited to casual wear and travel. Match the blue colorway with khakis or light-colored slacks and a matching polo. 

Material: Knit Silk | Sizes Available: EU 40 – 46 | Colors available: Navy, Dark Brown, Light Brown | Formality: Casual

Loro Piana 360 Flexy Walk Knitted Sneakers

What to Look for When Searching For The Most Comfortable Shoes

When it comes to picking out the most comfortable shoes for men, these are the prime considerations to keep in mind:

Material

First off, the material of the shoe is one of the largest factors influencing comfort. While leather shoes are typically the most durable and comfortable, they also have the longest break-in period. However, supple leather is designed to be gentle against the skin. So look out for this if you want to wear leather shoes right out of the box. 

If you’re looking for a softer, more sporty shoe, consider a mesh material. It’s much more breathable than leather, allowing those sweaty feet to feel the breeze every once in a while.

When it comes to the inner materials of a comfortable shoe, foam is a buzzword here. It provides a much-needed cushion between the foot and the ground. Though with foam comes a few tricks. Memory foam is always a tempting option because it molds to the foot but tends to have a shorter lifespan than other kinds. Choose a shoe with a higher density foam if you’d like it to last for years to come.

Person holding white hightop shoes and a basketball under arm
Clae / Instagram

Fit

The fit of a shoe should be snug enough that your foot doesn’t move around when walking, but with enough space to let those toes breathe. You should be able to comfortably wiggle your toes without them touching the front of your shoe.

It’s also worth considering a specialized fit if you have wide or narrow feet. Many of the most comfortable shoes for men come in wide or narrow sizes, so you can find the optimal fit. 

Don’t forget to keep an eye out for arch support, cushioned mid or insoles, and any specific sizing instructions for a particular shoe.

Style

Last but not least, it pays to consider the style of the shoe. Many of the most comfortable shoes for men are in the sneaker department, but there are plenty of dress shoes geared towards ease of wear. If you spend a lot of time commuting or on your feet at the office, a pair of comfortable dress shoes will serve you well. But if you’re looking for a pair of kicks to get you from Point A to Point B, sneakers are probably the way to go.  

FAQ

    • The most comfortable shoe brands include CLAE and Axel Arigato for casual wear and Myrqvist and Amberjack for dress shoes. That said, all brands on this list are geared towards comfortable footwear.

      • For daily use, Nike Air Max 90s are a great pick for a stylish option that’s easy to match with wardrobe basics. If you want slightly dressier shoes for daily wear, the Harlestone Derbies from Crown Northampton are versatile without sacrificing comfort. 

        • The most comfortable walking shoes include Saucony Triumphs, Asics Gel Ventures, and Hylo Run 2 sneakers. If you primarily walk on trails, the Salomon Speedcross sneakers are one of the most comfortable options for increased traction.  

          • When it comes to the most comfortable work shoes, it’s hard to beat any options from Myrqvist or The Originals by Amberjack. Other worthy contenders include Cole Haan’s Zerøgrand Wingtip Oxfords and Clarks Atticus leather dress shoes.





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