The 12 Most Comfortable Dress Shoes for Men
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
Best Overall: Ecco Men's Helsinki Comfort Loafers
Best Lightweight: Johnston Murphy Bradford Cap Toe Derby Shoe
Best Breathable: Clarks UnKenneth Way
Most Sizes: Rockport Modern Prep Penny Loafer
Best for Arch Support: Vionic Shane Oxford
Best Sneaker Substitute: Cole Haan Original Grand Wingtip Derby
Best Slip-on: Hush Puppies Men's Rainmaker Slip-on Loafer
Best Waterproof: Rockport Essential Details Waterproof Wingtip
Best Memory Foam: Samuel Hubbard 'Tipping Point' Wingtip Oxford
Best Luxury: Gucci Jordaan Leather Loafer
Best Budget: Dockers Edson Slip-on
Best Moisture-wicking: Florsheim Midtown Wingtip Oxfords
What to Look For When Buying Men's Dress Shoes
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."
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.