The 12 Most Comfortable Dress Shoes for Men
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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.
Our favorite is the Ecco Men's Helsinki Comfort Loafers for their sleek style and ultimate comfort; they're even moisture-absorbent to prevent odor.
Here, we've rounded up the best men's dress shoes that will keep you going and looking sharp wherever your business may take you.
- Best Overall: Ecco Men's Helsinki Comfort Loafers at Macy's
- Best Lightweight: Johnston Murphy Bradford Cap Toe Derby Shoe at Zappos
- Best Breathable: Clarks UnKenneth Way at Zappos
- Most Sizes: Rockport Modern Prep Penny Loafer at Amazon
- Best for Arch Support: Vionic Shane Oxford at Nordstrom Rack
- Best Sneaker Substitute: Cole Haan Original Grand Wingtip Derby at Nordstrom
- Best Slip-on: Hush Puppies Men's Rainmaker Slip-on Loafer at Zappos
- Best Waterproof: Rockport Essential Details Waterproof Wingtip at Amazon
- Best Memory Foam: Samuel Hubbard 'Tipping Point' Wingtip Oxford at Zappos
- Best Luxury: Gucci Jordaan Leather Loafer at Nordstrom
- Best Budget: Dockers 'Edson' Slip-on at Amazon
- Best Moisture-wicking: Florsheim Midtown Wingtip Oxfords at Zappos
Our Picks
Related Items
Best Overall: Ecco Men's Helsinki Comfort Loafers
These aren't called "comfort loafers" just for kicks; the Helsinki loafers are made for easy all-day wear. They're constructed with a padded tongue and collar and a built-in shock point for comfort, and they're even moisture-absorbent to keep feet dry and odor-free. They're also ultra-sleek, thanks to a soft, full-grain leather upper that comes in black or brown to suit your style. As a bonus, they're slip-ons, making airport security a breeze when you need to take them off.
Sizes: 5 to 16.5 | Material: Leather, rubber
Best Lightweight: Johnston Murphy Bradford Cap Toe Derby Shoe
Johnston Murphy is known for producing high-quality, lightweight dress shoes that are extremely comfortable, and this cap-toe derby shoe is no different. It's made with soft, breathable linings, a cushioned footbed, and a sophisticated round toe design with brogue detailing. The Bradford is also extremely light, weighing in at just one pound per shoe, which is about half the weight of the average men's dress shoe.
Sizes: 8.5 to 13 | Material: Leather, rubber
Best Breathable: Clarks UnKenneth Way
Made with high-quality leather, the lining of these shoes by Clarks is incredibly breathable — which makes the shoes perfect for everything from winter work commutes to summer weddings. Featuring a padded upper, a removable cushioned footbed, and a durable rubber sole for added traction, the shoes are a stellar option if you're looking for comfort and support.
Sizes: 7 to 15 | Material: Leather, rubber
Most Sizes: Rockport Modern Prep Penny Loafer
This classic pair of slip-on penny loafers from Rockport looks sleek both in and out of the office. The shoes have a stacked heel, a padded insole for shock absorption, and a lightweight feel that make them comfortable enough to wear all day long. One of the most interesting things about these loafers, though, is the number of available sizes. You can snag them in men's sizes 7 to 14, including half sizes, wide sizes, and even extra wide sizes.
Sizes: 7 to 14 | Material: Leather, rubber
Related: The Best Travel Shoes for Women Who Need Arch Support
Best for Arch Support: Vionic Shane Oxford
These water-repellant Oxfords by Vionic were specially designed by a podiatrist to provide ultimate comfort and orthopedic support. The shoes have removable leather-covered footbeds that mold to your foot's natural curves and help provide ample arch support. For added traction, each shoe boasts a durable rubber outsole.
Sizes: 7 to 13 | Material: Leather, rubber
Best Sneaker Substitute: Cole Haan Original Grand Wingtip Derby
These Cole Haan Derby shoes feature a segmented, flexible tread, a durable rubber outsole, a removable insole, and a cushioned footbed that work together to make them just as comfortable as your favorite pair of sneakers. And they even have a sporty look: while they do feature a classic wingtip on the toe, the thick, grooved heel gives them an unmistakable sneaker-like appearance.
Sizes: 6.5 to 16 | Material: Leather, rubber
Best Slip-on: 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. Not only is it missing the intricate toe design typical of similar loafers, but the Rainmakers are made sans laces, too — how easy can it get? They're even waterproof, so you can wear them for virtually any occasion. Just be sure to order on the smaller end of your size spectrum, as this pair tends to run large.
Sizes: 7 to 16 | Material: Leather, rubber, nylon
Best Waterproof: Rockport Essential Details Waterproof Wingtip
These shoes from Rockport are so stylish, no one would ever guess they're also incredibly functional. Not only are they completely waterproof, but they also feature a sponge-like footbed that contours to the wearer's foot shape, allowing for a perfectly personalized fit. Wear them in the winter or during a spring shower — either way, they'll keep you dry, comfortable, and fashionable.
Sizes: 5 to 16 | Material: Leather, vinyl
Best Memory Foam: Samuel Hubbard 'Tipping Point' Wingtip Oxford
Two words to describe this Oxford from Samuel Hubbard: comfortable and sturdy (the two traits you definitely want in a quality shoe). The triple-density memory foam insole offers comfort you've never experienced in a shoe before, and it'll keep your feet happy for hours on end. Plus, a durable rubber sole ensures these shoes will last a long, long time.
Sizes: 7 to 14 | Material: Leather, rubber
Best Luxury: Gucci Jordaan Leather Loafer
We love splurging on a good quality shoe every once in a while, especially when the shoe is Gucci — and in this case, the Gucci Jordaan Leather Loafer. The Italian-crafted shoes are made with fine leather lining, soles, and uppers, which offer comfort, flexibility, and durability. A gold-tone horsebit across each upper adds elegance, but because they're not too flashy, you can easily pair them with both formal wear and casual ensembles.
Sizes: 6 to 15 | Material: Leather
Best Budget: 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 Edson's sleek leather uppers, memory foam insoles, and moisture-wicking linings are sure to impress. A durable outsole also means the shoes will last through years of wear and tear.
Sizes: 7 to 15 | Material: Leather, rubber
Best Moisture-wicking: Florsheim Midtown Wingtip Oxfords
These timeless shoes are made with a specially developed moisture-wicking lining designed with comfort and breathability in mind, so you're sure to stay dry and odor-free on even the hottest and most humid days. Other features highlighted on these Oxfords are removable cushioned footbeds, flexible rubber outsoles, and sophisticated brogue detailing.
Sizes: 7 to 14 | Material: Leather, rubber
What to Look For When Buying Men's Dress Shoes
Comfort
Apart from choosing the proper size, a quality footbed or insole is typically the difference between a comfortable and uncomfortable shoe. Look for pairs that boast padded, cushioned, or memory foam footbeds, like many of the picks above. According to podiatrists, shoes that match your foot shape can also work wonders. "For example, if you have a bunion making your forefoot wider and more square, then avoid shoes that have a point or are more narrow in the toe box," says Dr. Jacqueline Sutera of City Podiatry in New York City. "Accommodate the forefoot with materials made of mesh or a soft, forgiving leather."
Style
If you plan to wear your dress shoes strictly in professional settings like work or formal events, stick to styles like Oxfords and derby shoes with a slight heel. If you're going for a slightly more casual dress look, consider less formal options like loafers with thick, sporty soles.
Frequently Asked Questions
How should dress shoes fit?
Your feet shouldn't completely fill the shoe. If you're standing straight up with your dress shoes tied and your heels pressed against the back, your toes should not touch the front of the shoes. In fact, there should be roughly half an inch of space there. Your pinky toe's comfort is also indicative of a good-fitting shoe: if it feels a bit crammed in the shoe, you should size up or choose a wide width version of the shoe, if it's available. And, of course, if the shoes slip off your feet when you walk, you'll need a smaller size.
How do you break in dress shoes?
Break in your new shoes by wearing them for short periods of time to start, whether that's around the house or on short walks. To avoid blisters during the break-in period, place bandages or other padding on spots that rub early on, and wear them with a quality pair of socks. Skip doing anything extreme to speed up the process, like heating the shoes or sticking them in a washing machine; that will likely end up doing more harm than good.
Why Trust Travel + Leisure
Travel + Leisure writers are shopping, fashion, and product experts who use personal experience and customer recommendations to choose the best items for shoppers. For this article, editors Rebecca Carhart and Hillary Maglin researched dozens of men's dress shoes and used their expertise as seasoned home, fashion, beauty, and lifestyle writers to curate the perfect list of comfy, durable, and stylish dress shoes for men.