Skip to main content

The Most Comfortable Work Shoes for Any Environment, From Back of House to Board Room

If you get home from work with an aching back or stiff neck, headaches, and digestive issues, or just feeling disproportionately tired, the culprit could well be your feet. More specifically, what you’re wearing on them. Poorly fitting shoes cause more than just blisters. They lead to over-pronation, an issue that leads to a host of common afflictions, such as heel pain (plantar fasciitis), knee pain and lower back pain. They affect the way your body moves and stands, putting undue pressure on the back, hips, ankles, and knees.

Let’s face it—you’re too young to be groaning about your aches and pains, and too ambitious to spend your workday dreaming of your La-Z-Boy. Our list of most comfortable men’s work shoes will keep you both spry and stylish, no matter where or how you earn your living.

Recommended Videos

Formal Office

Buy at Amazon
Vionic’s Bruno Oxford
Image used with permission by copyright holder

The upper tiers of society have a long-standing habit of dressing as if they’ve never done a day’s work in their lives, and never will. But if you’re working a white-collar job, you know that facade is far from true. For the past 50 years or so, the wingtip oxford has been the equivalent of ancient China’s extra-long fingernails or the starched collar of the early 19th century—as uncomfortable as it is iconic. Fortunately, Vionic has come to the rescue with a sophisticated oxford that won’t outrage your podiatrist. A super supportive footbed and a durable rubber sole keep your feet cushioned, while contrast stitching and optional contrast laces give the undeniably stuffy silhouette a needed facelift.

Buy at Amazon

Casual Office

Buy at Allbirds
Allbirds Wool Runners
Image used with permission by copyright holder

There’s a lot that’s problematic about startup culture, but one thing it definitely has going right is its footwear. Make like the bigwigs of the new economy and suit your feet up in Allbirds. These sneaks and slides are not only cozy, minimalist and sustainable, they’re also ridiculously comfortable, with uppers and padded insoles made from the same superfine merino used for Armani suits, and a low-density outsole featuring a unique S-curve tread array designed to mimic the anatomical flexibility of your feet and provide natural weight distribution. The reviews you’ve read online may sound hyperbolic (e.g., “they’re like slippers made of clouds”), but we swear the hype is true. Just ask the Allbirds army of fans, which includes a slew of Silicon Valley titans, Hollywood icons such as Woody Harrelson and Leonardo DiCaprio, and even former (sniff!) President Barack Obama.

Buy at Allbirds

Courier/Active/Assistant

Buy at Amazon
Nike Roshe One
Image used with permission by copyright holder

When your job keeps you running—be it all over town, or all over the gym—you need a shoe that performs like a sports star. At the same time, you don’t want to be the guy in chunky cross-trainers, especially amongst a lot of well-heeled types who depend on your services—that’s no way to get your big break. The streetwear styling of the Nike Roshe One gives you a look that’s on the level with anyone you’re training/delivering to/getting coffee for, while the soft lightweight sole, cushioned collar and traction-heavy waffled outsole lend them to heavy lifting and quick maneuvering. They’re the perfect shoes for climbing your way to the top.

Buy at Amazon

Retail/Fashion Industry

Buy at Amazon
Saucony Jazz Low Pro
Image used with permission by copyright holder

With apologies to Derek Zoolander, effortlessness is the essence of looking cool. But if you’ve ever worked retail, you know it means long hours on your feet, not to mention a lot of jumping, reaching and squatting. Other careers in the fashion industry are similarly athletic. A pair of Saucony Jazz Low Pro sneakers are the key to keeping it pulled together. Their slim fit, plush suede outer, and retro styling in a plethora of colorways keeps your look fresh and fly; nobody has to know that the cushioning insole, shock-absorbing midsole, and rubber traction outsole are saving your life.

Buy at Amazon

Food and Beverage Industry

Buy at Amazon
Image used with permission by copyright holder

Like other models in the Scarpa catalog, the best-selling Mojito was designed as a climbing shoe. But its sweet Euro profile and deliciously comfortable construction have made it a streetwear staple. We think this combo makes it the perfect pick for bartenders, servers, and F&B employees at every level. Vibram soles are skid-resistant, a reinforced arch offers comfort and support, and Italian leather uppers keep the look classy. What’s more, the Scarpa Mojito comes in every color and shade you can imagine, which means you’re guaranteed to find a perfect match with your work uniform.

Buy at Amazon

Construction/Labor

Buy at Amazon
Image used with permission by copyright holder

Fashioned from Red Wing’s signature oil-tanned leather, the Iron Ranger boots not only resist water, stain and, perspiration but look good doing it. With a steel shank, double-layered toe, Vibram 430 Mini-lug outsole, and Goodyear welt construction, these 6-inch boots are tough on the outside, but gentle on the inside, thanks to a cushiony cork midsole and a bump toe for more room up front. No wonder Style No. 8111 has been the choice of hard laborers since the days of Minnesota’s mining boom.

Buy at Amazon

Outdoor Industries

Buy at Amazon
Keen Austin Casual Boot
Image used with permission by copyright holder

The legendary Austin boot from Keen gets a little classed up, while maintaining the shoe’s renowned outdoor performance. The carbon rubber sole, metatomical footbed, and Cleansport NXT odor control technology give you all the sturdy support of a trail boot, while the full-grain nubuck leather upper says, “I’m at work.” Wearing the Keen Austin boot means you can go from guiding tours of a national park to giving a keynote speech to important donors a date with a cute tourist with no change of footwear required. Just don’t go logging in these.

Buy at Amazon

For those of you who only work outside and with your hands, you’re going to need a heavy boot for that. Why not try one of our top picks for best work boots and feel the comfort of elevated work boots yourself.

Chelsea Batten
Former Former Digital Trends Contributor, The Manual
Chelsea Batten is a writer, photographer, and Kerouac groupie. One of the original digital nomads, she was seduced from life…
Topics
Experience next-level style with HOKA’s futuristic Mach X Caged
HOKA's new Mach X Caged adds sculptural design to a performance shoe
green hoka mach x caged

As HOKA continues to push the boundaries between style and performance, its latest Mach X Caged release blends the needs for comfort and design. Like other brands, HOKA’s approach takes on a sculptural look, making it easier for users to wear this sneaker beyond the track. Similar to Adidas’ Climacool 3D sneaker, this HOKA piece infuses translucent details to create a sheer, see-through effect that elevates the typical sneaker into a piece of art. While this shoe is crafted with a new modern look, the technical aspects of the sneaker remain similar to the rest of the Mach lineup. Available in two colorways, Pea Green/Hoka Citrus and Black, the HOKA shoe is a contemporary approach to a classic shoe. 

HOKA’s Mach x Caged blends design and performance

Read more
Inside Cole Haan’s most technologically advanced shoes to date
Cole Haan's Fall 2025 collection is here - and it's their most advanced release yet
cole haan wingtip oxfords

When it comes to dress shoes that are comfortable for all-day wear, no brand does it quite like Cole Haan. Notorious for their ability to blend timeless and stylish looks with a cushion that doesn’t hurt, Cole Haan is getting ready for fall in the only way they know. As part of their new Fall 2025 campaign, Cole Haan is not only introducing a series of silhouettes apt for the season, but is delivering the most innovative designs in their history.  As stated by Cole Haan’s Chief Creative Officer, Scott Patt, “Fall 2025 is designed for real life and all its unpredictability. From revolutionized oxfords to engineered sneakers to weather-ready boots, we’ve created beautiful, smart products that help you show up, stay present, and feel great while doing it.” Under the campaign name of “Cole Haan Comfortable,” this season’s upcoming collection is made for formal and casual events, and everything else in between. 

Get comfortable with Cole Haan’s Fall 2025 campaign

Read more
KEEN makes golf debut with Metalwood Studio shoe collection
KEEN and Metalwood Studio gear up for the brand's first golf footwear
KEEN metalwood studio shoe

While KEEN is primarily known for its outdoor shoe lineup that adds performance details to rugged footwear, it doesn’t mean that the brand is shutting itself off from other types. As golf continues to grow as a sport and as a style, it's no surprise that KEEN has opted to dabble in golf footwear for the first time. Along with LA-based streetwear brand Metalwood Studio, KEEN is making its mark on the green. In this new collaborative collection, the duo is releasing two new golf shoes that are crafted for pre- and post-games. Although most of KEEN’s lineup is already suited for any outdoor activities, these golf-specific options offer fans of the sport a designated choice that brings together KEEN’s performance technology and Metalwood Studio’s knowledge of the game. 

KEEN and Metalwood Studio’s first joint appearance on the green 

Read more