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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.

Formal Office

Vionic’s Bruno Oxford
Vionic’s Bruno Oxford
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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.

Casual Office

Allbirds Wool Runners
Allbirds Wool Runners
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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.


Nike Roshe One
Nike Roshe One
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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.

Retail/Fashion Industry

Saucony Jazz Low Pro
Saucony Jazz Low Pro
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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.

Food and Beverage Industry

Scarpa Mojito
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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.


Red Wing Style No. 8111 Iron Ranger Boots
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.

Outdoor Industries

Keen Austin Casual Boot
Keen Austin Casual Boot
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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.

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.

Editors' Recommendations

Chelsea Batten
Former Digital Trends Contributor
Chelsea Batten is a writer, photographer, and Kerouac groupie. One of the original digital nomads, she was seduced from life…
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