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: nordstrom.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 loafers from La Milano 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. Plus, they come in seven stylish colors.

To buy: amazon.com, from $50

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

“It truly is like wearing running shoes disguised as the perfect-looking dress shoe,” stated one reviewer of the Cole Haan Washington Grand Laser Wingtip Oxford. And it certainly doesn’t get more comfortable than a pair of sneakers.

To buy: colehaan.com, $400

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: amazon.com, from $106

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: zappos.com, $100

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: nordstrom.com, $245

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

To buy: nordstrom.com, $730

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: zappos.com, $50

A more budget-friendly option for the wingtip oxford is this smart pair from Florsheim. At just $100, these timeless shoes are made with a leather lining added specifically with comfort and longevity in mind.

To buy: macys.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 241 five-star reviews this pair received.

To buy: macys.com, $150