The Most Comfortable Dress Shoes for Men
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.
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 10 of the best men’s dress shoes that will keep you going and looking sharp wherever your business may take you.
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 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 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 ‘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
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
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 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 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 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.
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.
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.