The 17 Most Comfortable Dress Shoes, Tested by Style Editors

Loafers generally err on the side of comfortable, but some have a tendency to cut up your heels and pinch your toes. Tod’s loafers are not those loafers. The brand put many of the same details from their beloved driving shoes into these penny loafers like the pebbled rubber sole for grip and the smooth and flexible leather upper.

One customer said: “The craftsmanship is outstanding, with high-quality leather that feels luxurious and durable. The fit is perfect, providing excellent comfort for long hours of wear. The elegant design is timeless and pairs well with both formal and semi-formal attire.”

We’re calling the Gucci Horsebit 1953 Loafer one of the official favorite shoes of Esquire. We’ve waxed poetic about several Gucci loafers but this version is worthy of another level of praise. From its high-quality craftsmanship to its versatility and ability to pair with almost everything in your wardrobe—our particular favorite is a jeans, blazer, and loafer trifecta—this shoe instantly elevates. And, yeah, it’s very comfortable, too.

The first word to describe Mephisto’s wingtip derbies is durable. The stacked rubber sole with shock absorption is a solid choice for avoiding foot pain. If you plan to stand for hours, these will deliver just the right amount of support without feeling overly clunky. The textured full-grain leather upper is certainly a style preference, but a classic one—and there’s a black version, too.

One customer said: “Outstanding and durable dress shoes—I’ve had mine for a decade and they are still going strong. Take care of them, they take care of you. After 12 hours my feet still feel great. Awesome product!”

Chukka boots can lean casual, but these high-gloss leather boots are as sleek and sophisticated as they come. The soles have been hand-painted to match the upper for a seamless look. The inside is also lined in leather, for even more softness for your hard-working feet. These come in five leather colors and three suede options.

One customer said: “I am constantly getting compliments when I wear these shoes. The color and design are incredible. This is my third pair of Paul Evans and are quickly becoming my favorite. The fit was perfect and they are extremely comfortable. You can’t go wrong with the Newman Chukka! The experience of ordering and shipping are always excellent.”

Monkstraps are a little offbeat, but still a classic alternative to derbies or oxfords. These stunners are made to order and come in five colors. The temperature-regulating leather lining keeps your feet from overheating, and then there’s a steel shank sandwiched between the inner and outer soles for added support while standing. The quality and details are top-notch all around.

One customer said: “I continue to be blown away by these shoes every time I wear them. The quality is simply outstanding. I was somewhat nervous about how these would hold up to standing at work for 10 hours a day but they are super comfortable. On top of the quality and comfort they just look great. Excited to wear these shoes for a very long time and add some other Beckett Simonon options to the lineup soon.”

Sometimes the best dress shoe is the simplest dress shoe. Case in point, this plain-toe blucher. If your dressy occasion ends up being a soggy one, the good-year welt stitching around the sole will keep any bits of moisture out. The double leather soles are flexible and durable, and adds the right amounts of cushioning for comfy walking and dancing.

One customer said: “This is the perfect shoe: dress it up or dress it down. And, comfortable to boot!”

These are super classy and a little unique, too, with a slightly squared-off toe. Wear them with everything from trousers to a suit. The stacked heel, padded insole, and rubber outsole are ideal for flat feet that need arch support—but it doesn’t make them clunky or heavy. They’re still very lightweight and flexible.​

One customer said: “I love that Stuart Weitzman is making men’s shoes now, and these classic Oxfords definitely deliver. They’re comfortable for all-day wear and go with everything I already have in my closet. They’ve become a staple in my wardrobe, and I reach for them anytime I need an elevated shoe.”

The almond toe shape on these Ferragamo loafers up its dressiness level from a classic loafer. The rubber sole makes standing in these loafers more comfortable and they are available in three different widths, so if you like the narrower look but have a wider foot, pick accordingly. There’s a note that they run large so you may need to size down a half size.

G.H. Bass is the OG of the penny loafer—one that’s made many of our lists here at Esquire. The brand’s beefroll-style loafer is iconic. The shoe features a leather upper, moc stitching around the toe, and a stacked heel. It comes in medium and wide widths and a bunch of colors, too.

One customer said: “This is the only dress shoe I wear. G.H. Bass just knows what they’re doing when it comes to timeless footwear that will last you for years, dare I say even decades? This style is classic, versatile, and incredibly durable. So basically, anything you could ever want in a shoe.”