The Most Comfortable Dress Shoes for Men

Johnston Murphy has been a popular shoe brand since 1850 for a reason. It is known for producing high-quality, lightweight dress shoes that are extremely comfortable, and this cap-toe derby shoe is no different. One happy customer wrote, “Shoe is very comfortable. Lightweight and very elegant looking.”

To buy: zappos.com, $130

These stylish dress shoes by Clarks feature a breathable leather lining and padded leather upper for extra comfort and support. They also have a cushioned footbed that is removable and a durable rubber sole for added traction.

To buy: zappos.com, $160

This sleek pair of slip-on penny loafers from Rockport will look good both in and out of the office. The shoes have a stacked heel and padded insole that make them comfortable enough to wear all day long. “These are the most comfortable dress shoes I own. So happy I found them,” wrote one shopper.

To buy: nordstrom.com, $90

This smart-looking pair of oxfords by Vionic was specially designed by a podiatrist to provide ultimate comfort and orthopedic support. It also has a removable leather-covered footbed that helps provide ample arch support and a rubber outsole for great traction.

To buy: zappos.com, $150

These Cole Haan Derby shoes feature a flexible tread, durable rubber outsole, and an anatomically engineered footbed that work together to make these dress shoes just as comfortable as your favorite pair of sneakers. Seriously, one shopper said, “Feels like I’m wearing my running shoes. I can wear them all day without any issues.”

To buy: nordstrom.com, $160

Not a wingtip kind of guy? Hush Puppies’ slip-on loafer might just be your new favorite dress shoe. No laces to deal with and they’re waterproof — how easy can it get? Just be sure to order on the smaller end of your size spectrum, as this pair tends to run large.

To buy: zappos.com, $135

Using sport technology in the heel area for shock absorption, Rockport created the ideal men’s dress shoe for just $100. This pair even comes in two different colors: classic black, and a rich shade of burgundy.

To buy: nordstrom.com, $100 (originally $110)

Two words to describe this oxford from Samuel Hubbard: classic and sturdy (the two traits you definitely want in a quality shoe). Plus, the Vibram Morflex rubber sole and the memory-foam insole will keep your feet happy for hours on end.

To buy: zappos.com, $275

Designed with an elongated toe to complement the quality Italian leather Gucci is known for, the Jordaan leather loafer is both a dress shoe and a wardrobe staple. Pair with a striped sock (or your favorite funky pattern) and go from the office to the dance floor without changing your footwear.

To buy: nordstrom.com, $850

The least expensive pair of dress shoes on our list certainly doesn’t sacrifice comfort for price. If you aren’t quite ready to invest, but still want to look and feel good, the Dockers slip-on is the way to go.

To buy: amazon.com, from $50

A more budget-friendly option for the wingtip oxford is this smart pair from Florsheim. At just $110, these timeless shoes are made with a moisture-wicking lining added specifically with comfort and breathability in mind. “Super comfortable. The first time I wore them was to a wedding. After almost 11 hours of use they still felt great. Definitely worth paying a little more for a quality shoe,” wrote one customer. 

To buy: zappos.com, $110

They’re not called “Comfort Loafers” just for kicks. This pair from Ecco is truly made for all-day (and all night) wear. Don’t believe us? Check out the hundreds of five-star reviews this pair received.

To buy: macys.com, $160