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The Most Comfortable Dress Shoes for Men

Comfortable Men's Dress Shoes Travel

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There should be at least one pair of reliably comfortable, stylish dress shoes in every man’s closet. LYDIA MANSEL OCTOBER 23, 2018Each 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.

It may be a cliche, 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.

RelatedComfortable 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 10 of the best men’s dress shoes that will keep you going and looking sharp wherever your business may take you.

Cole Haan Wingtip Oxford Shoe

Courtesy of Cole Haan

Cole Haan Washington Grand Laser Wingtip Oxford

“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

Hush Puppies Slip-On Loafer

Courtesy of Amazon

Hush Puppies Men’s Rainmaker Slip-on Loafer

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 $125

Rockport Waterproof Wingtip

Courtesy of Zappos

Rockport Essential Details Waterproof Wingtip

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

Samuel Hubbard Wingtip Oxford Shoe

Courtesy of Nordstrom

Samuel Hubbard ‘Tipping Point’ Wingtip Oxford

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

Gucci Jordaan Leather Loafer

Courtesy of Farfetch

Gucci Jordaan Leather Loafer

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: farfetch.com, $730

Dockers Edson Slip-On Dress Shoe

Courtesy of Zappos

Dockers ‘Edson’ Slip-on

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

Florsheim Marino Wingtip Oxford Shoe

Courtesy of Macy’s

Florsheim Men’s Marino Wingtip Oxfords

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

Ecco Comfort Loafers

Courtesy of Macy’s

Ecco Men’s Helsinki Comfort Loafers

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

Wolf & Shepherd Onyx Wingtip

Courtesy of Wolf & Shepherd

Wolf & Shepherd Senna Onyx Wingtip

No excess weight has been added to this dress shoe option from Wolf & Shepherd, thanks to its lightweight carbon-fiber arch support. Even with the addition of a sheepskin footbed lining, the Wingtip is advertised as averaging a pound lighter than other makes

Best Dress Shoes For Men This Spring That Are Stylish And Comfortable

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There are a variety of modern and on-trend dress shoes that are currently available on the market, such as brogues, wingtips, and loafers. Some provide extra comfort for those long days on your feet at the office. Others are weatherproof and waterproof protecting you from those unexpected spring showers on your daily commute. And finally, there are those statement dress shoes with unique details that are perfect for the theater, a night out with your lady, or an evening soiree.

But, how do you narrow down the options? When it comes to dress shoes, price point is important. However, making an investment in the right shoe could seamlessly take you through each season without significant wear and tear.

We have conducted our research and compiled a list of our favorite dress shoes for men. (We’ve also compiled lists of the best shoes for women, and sneakers for women and men this season.)

Cole Haan ‘Warren’ Cap Toe Derby

Derby shoes are a timeless classic and are perfect to wear to the office.  This stylish shoe is designed for comfort with Cole Haan’s proprietary Grand OS technology. The shoe features a lace up style, cap toe, and a cushioned rubber sole. It comes in two colors, Black and British Tan Leather.


Magnanni Marco Monk Strap Loafer

Looking for a convenient and striking shoe to wear on your upcoming interview? Then, consider this fashionable loafer from Magnanni. The shoe features unique stitching and an antique finish buckle closure.  Crafted in leather, the shoe provides a flexible fit for added comfort.


For the guy who appreciates luxury, this Gucci shoe is a great option. Designed by the coveted Gucci fashion house, this pair of loafers is crafted in supple Italian leather. The shoe features a charming signature ‘GG’ placed on the upper band. The band either comes in solid colors or features the signature Gucci grosgrain ribbon.