8 Comfortable Work Shoes for Men

Aug 14, 2023

Including discounted pairs from Johnston & Murphy and Cole Haan.

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Travel + Leisure / Daisy Rodriguez

Traditional dress shoes can be literal pains, and the last thing you need during a busy day at work is a blister. My dad’s been wearing these his whole career, but he recently discovered a new type of work shoe that’s seriously upgraded his wardrobe — and alleviated foot pain: the Johnston & Murphy Upton Plain Toes Oxford Shoes. These kicks combine fashion and function: they’re stylish dress shoes made from high-quality materials like leather and sheepskin, but they have flexible, sneaker-like rubber tread for a more comfortable commute (my dad often bikes to work in his Johnston & Murphy Oxfords, and he loves that he doesn’t need to lug an extra pair of shoes to change into when he gets to the office).

To give your feet a break on your next work trip (or even during your regular 9-to-5), we've rounded up some of the best comfortable dress shoes from retailers like Amazon, Zappos, and Nordstrom Rack. Best of all, most are on sale — starting as low as $37 — and these supportive styles can easily be incorporated into your travel and everyday wardrobes.

Zappos

These classic lace-up dress shoes are made with soft, full-grain leather and feature cushioned insoles for comfort. Plus, their synthetic soles are grippy and lightweight for an easier walk to work. One Zappos customer shared, “I love the all-day comfort from this lightweight dress/casual shoe that pairs with everything from slacks to blue jeans." They’re available in men’s sizes 8 to 13 and come in a range of shades, including brown, black, gray, and blue.

Amazon

Made with 100 percent leather uppers, EVA midsoles, and rubber outsoles, these wingtip Oxfords have attractive stitching and brogueing details that make them just as stylish as they are supportive. As one businessperson, who admits to standing for 90 percent of their workday, wrote, “These are the most comfortable dress shoes I have owned. There is very little break in [needed], they are lightweight, and I feel like I am wearing a pair of running shoes all day.” They’re available in a bunch of color combinations, ranging from traditional brown and black hues to camouflage and flowers. What's more, they come in half sizes and two widths: regular and wide.

Zappos

Made with soft sheepskin linings, Italian vachetta leather uppers, and sturdy rubber soles, these Johnston & Murphy shoes have a unique woven texture that will make them stand out among the other footwear in your collection. The lace-up kicks also have removable foam footbeds, and they’re available in men’s sizes 8 to 13. Choose between black and tan for a sleek, classic look.

Amazon

A budget-friendly pick, these faux leather dress shoes have cushioned memory foam footbeds, anti-slip soles, and breathable fabric linings for comfy, all-day wear. One fan shared, "I find them to be exceptionally comfortable, especially considering the affordable price." Their laser-cut detailing adds some texture and flair to the toes and sides, and you can choose between black, navy, and two shades of brown. They come in men’s sizes 5 to 13.

Johnston & Murphy

While this leather pair truly looks like a classic pair of dress shoes — thin laces and all — the outsoles are remarkably flexible and grippy to ensure a painless commute to work, according to my dad. Similarly, a Zappos shopper declared that they “may be the most comfortable, best-looking semi-dress shoes ever." It's also worth noting that the footbed is removable, and the shoes feature convenient heel tabs so getting them on and off is a breeze. We appreciate that they come in two widths, medium and wide, multiple colors, and sizes up to a men’s size 16.

Johnston & Murphy

These leather dress shoes have cushioned EVA footbeds and sturdy rubber-like outsoles for excellent arch support, traction, and stability. Plus, they have neoprene collars for a comfortable fit at the ankles, and we love the sophisticated stitching details. The versatile shoes “can be worn for various occasions,” one wearer noted, adding that they travel frequently for work. They’re available in tan or gray, and they come in men’s sizes 8 to 13.

Amazon

With faux leather details on the heels and tongues, these dapper Oxfords have knit uppers that contours to your feet. The style is a little more casual than most leather options, so they might be reserved for casual Fridays or vacation wear — but, they make excellent summer dress shoes because of their breathability. This Cole Haan pair is available in three classic colors at Nordstrom Rack, where they're up to 45 percent off. Hurry, certain sizes are already starting to sell out.

Zappos

Featuring temperature-regulating polymer linings, these full-grain leather kicks have flexible grooved soles for all-around walking comfort. The footbeds are cushioned with memory foam for ultimate support, and the cozy, quick-drying sheepskin-microfleece linings will feel great against your skin. The shoes come in a striking navy blue color that can be dressed up or down. Sizes range from 8 to 13.