The Most Comfortable Dress Shoes for Men

By Lydia Mansel and Rebecca Carhart
Updated July 20, 2020
Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.
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It may be a cliché, gentlemen, but it’s still important: Life is all about putting your best foot forward.

And when we say “best foot,” we mean a foot that’s clad in a stylish and comfortable dress shoe, when appropriate. Whether you’re spending countless hours in meetings and presentations or you have to attend wedding after wedding this year, a comfortable men's dress shoe is a wardrobe necessity.

Related: Comfortable Dress Shoes for Women

Fortunately, finding the right dress shoe is relatively simple. All you really need is one pair in a neutral color, crafted with quality materials and solid sole support.

Here, we’ve rounded up 12 of the best men's dress shoes that will keep you going and looking sharp wherever your business may take you.

These are the most comfortable dress shoes for men:

Johnston Murphy Bradford Cap Toe Derby Shoe
Clarks UnKenneth Way
La Milano Double Monk Strap Slip on Loafer
Vionic Shane Oxford
Cole Haan Washington Grand Laser Wingtip Oxford
Hush Puppies Men’s Rainmaker Slip-on Loafer
Rockport Essential Details Waterproof Wingtip
Samuel Hubbard ‘Tipping Point’ Wingtip Oxford
Gucci Jordaan Leather Loafer
Dockers ‘Edson’ Slip-on
Florsheim Men’s Marino Wingtip Oxfords
Ecco Men’s Helsinki Comfort Loafers
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Johnston Murphy Bradford Cap Toe Derby Shoe

nordstrom.com

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

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Clarks UnKenneth Way

zappos.com

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

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La Milano Double Monk Strap Slip-on Loafer

amazon.com

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 $65

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Vionic Shane Oxford

zappos.com

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

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Cole Haan Washington Grand Laser Wingtip Oxford

Courtesy of Cole Haan

“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: zappos.com, $291 (originally $400)

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Hush Puppies Men's Rainmaker Slip-on Loafer

Courtesy of Amazon

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 $75

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Rockport Essential Details Waterproof Wingtip

Courtesy of Zappos

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 (originally $110)

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Samuel Hubbard ‘Tipping Point’ Wingtip Oxford

Courtesy of Nordstrom

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, $265

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Gucci Jordaan Leather Loafer

Courtesy of Nordstrom

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, $730 (originally $790)

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Dockers ‘Edson’ Slip-on

Courtesy of Zappos

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 (originally $75)

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Florsheim Men's Marino Wingtip Oxfords

Courtesy of Macy's

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

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Ecco Men's Helsinki Comfort Loafers

Courtesy of Macy's

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

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By Lydia Mansel and Rebecca Carhart