The Most Comfortable Shoes for Men, Tested by Style Editors

As a style editor, I’ve slipped my foot into a number of shoes, but Cole Haan churns out the most comfortable pair across the board. Take the GrandFlex Dress Cap Toe Oxfords, which arrives in black, dark brown, and a sleek mahogany. Most dress shoes require a rough break-in period, but I didn’t have that issue here. This pair’s insole molds to the shape of your foot and feels snug right off the bat. The overall design construction is super lightweight with FlowerFoam midsole, a proprietary material made from dandelion rubber, which provides a soft yet springy support.

Since they’re not super bulky and have excellent cushioning, I’ve worn them for city commutes and travel days through the airport. They’re especially comfy for hours at a time, if you have a standing desk at work or attend a networking conference. In terms of style, Cole Haan’s offering looks great with business formal attire; think a little suit and tie moment. You can also go for a smart-casual look for date night and pair it with black jeans and a lightweight sweater—so there’s lots of versatility here.

Read More: Most Comfortable Dress Shoes

Pros

• Works for long-distances and quick strolls
• Softens the impact of each step
• Meta-Rocker technology helps your foot roll forward naturally

Our fitness editors log an average of 20 miles per week, and they swear by these Hoka running shoes for everything from pounding the pavement to crushing treadmill runs. The lightweight silhouette has more cushioning than previous iterations, so you get a soft, bouncy feel without the extra bulk. One of the standout features is the Meta-Rocker technology, which is a fancy way of saying the shoe is designed to help your foot roll forward naturally with each stride. This reduces strain on your legs over long distances.

We’ve put the Clifton 9 to the test for the New York marathon and, while extensive runs like that can be tough on your feet, this shoe didn’t cause any pain—no blisters, no sore spots, just consistent comfort all the way through. The midsole is made from compression-molded EVA form, meaning it softens the impact of each step—great for anyone who runs on hard surfaces like concrete or a treadmill. For extra comfort, the upper part of the shoe is updated with a breathable mesh, keeping your feet from being sweaty or feeling too tight. Performance aside, these sneakers are perfect for recovery walks, store errands, and even all-day wear on hard city streets.

The Original uses a custom TPU outsole that is both durable and comfortable, which gives you a solid base while still offering sneaker-like flexibility, so you can move easily and comfortably all day long. The recessed heel enhances cushioning, and our testers found it also gives a bit of added bounce, like you’re walking on clouds. What really sets this shoe apart is the proprietary outsole that provides traction, thanks to the that keeps you from falling on slick city streets or transitioning from indoor and outdoor environments.

Beyond the performance, the shoe is crafted from full-grain leather or Italian suede—a luxurious, high-end look, while still being practical. It’s also water-repellent, so light drizzles or spills won’t ruin your look. Inside, you’ll find a buttery-soft sheepskin lining, adding extra comfort and breathability to prevent your feet from overheating. They’re perfect for a wedding, yet comfortable enough for a casual dinner or even a weekend getaway.

If you’re someone who enjoys morning strolls and or quick walks to the coffee shop for your daily pick-me-up, the Brooks Addiction Walker might just be your new best friend. These shoes come with BioMoGo DNA cushioning, a midsole that adapts to your foot’s shape and walking style, for personalized support. This cushioning absorbs impact, reducing pressure on your joints, making it great for longer walks. Equipped with a progressive diagonal rollbar located in the midsole, the shoe guides your foot’s natural motion, offering extra stability. This feature is especially helpful for anyone with flat feet or if your feet tend to roll inward while walking.

Yes, they might give a dad-shoe vibes, but that doesn’t cancel out their comfort. Nonetheless, the cushioning is top-notch, and the high-traction rubber outsole ensures a firm grip, which is great for both wet and dry conditions, preventing slip and falls. And when it comes to comfort, the supple leather upper is soft and flexible, molding to the shape of your foot over time, offering a snug yet comfortable fit.

A comfortable shoe that can be worn to a summer wedding, the office, and casual outings is a winner. Take Peter Millar’s penny loafer. I’ve worn it with a tailored suit to a loved one’s nuptials, but I’ve also found it looks chic with a polo shirt and linen pants for a resort dinner. To be clear, the shoe doesn’t have to be reserved for super formal occasions—it pairs just as well with jeans for a laid-back fit. The rubber outsole gives you that nice bounce with every step, so it’s not stiff or clunky.

You get a bit of cushioning but still plenty of support, making it feel like you’re gliding along instead of trudging. Construction-wise, it’s made with water-resistant suede, treated to repel moisture, which makes it more resistant to water damage compared to regular suede. While it’s not fully waterproof, it offers added protection against rain and light spills. Just don’t wear it to an overly crowded festival where someone might step on your foot.

The Puma MagMax NITRO is hands-down one of the most comfortable performance shoes I’ve ever worn. It’s one of my go-to’s for my Barry’s workout classes that consists of floor exercises and treadmill runs. That’s because the NITRO foam cushioning is next-level—super light, insanely responsive, and it gives you that perfect mix of bounce and support without feeling too squishy.

The first time I laced these up, I noticed how effortless each step felt, whether I was doing sprints, cutting side to side, or just walking around post-workout. The PUMAGRIP outsole? It’s got unbeatable traction that grips the ground like glue, whether you’re on slick gym floors, pavement or even slightly wet surfaces.

During my testing, I could feel each step was secure and stable—no second-guessing my footing, just smooth controlled movement. When I’m not wearing these shoes with a workout shirt and gym shorts to hit my PRs, I pair them with a simple tee and joggers for grocery runs or dog walks.