Our product picks are editor-tested, expert-approved. We may earn a commission through links on our site.
From suede loafers to classic wingtips.
THERE ARE a few items that every man should have in his closet. A well-fitting suit. A go-to pair of jeans. A solid winter coat. One of the most important essentials: comfortable dress shoes. Dress shoes are one of those items that, sure, you might not wear every day. But when it comes time to wear them, there is no alternative. Sneakers and a suit can be fun, but they're not always job interview or wedding material.
It's also a wise idea to look at dress shoes—or even purchase them—before you need to wear them. Trying to find an emergency pair of dress shoes before a big event means your options might be limited, or you could get stuck with a pair that needs a few wears of breaking in. Shopping for comfortable dress shoes now means you can avoid the stress (and blistered heels) that come with panic shopping.
Dress shoes don't have to be expensive or complicated, either. It's nice to have a pair of black and a pair of brown, and a pair of lace-ups and slip-ons. If you don't like feeling stuffy, you can opt for hidden cushy soles or even a pair of streamlined boots. Here are 20 of the most comfortable dress shoes for men on the market.
An Oxford is the OG dress shoe, with a closed lacing for a streamlined silhouette. If you're looking for a dress shoe that feels like a sneaker, Cole Haan's dress shoes have you covered. This option has a hyper-cushioned rubber sole so your feet feel supported.
Read more: Best Shoes for Men
When mixing up your dress shoes, sometimes no laces is the way to go. Monk Strap shoes are secured by a single strap or a double strap and buckle, like these Beckett Simonon shoes. They are traditionally less formal than an oxford shoe, but can still be a dressy option for work.
Urban dwellers can’t just stick with the same pair of old-school dress shoes when having to splash through the dreary, rainy days that lead the change of seasons. Keep your fine Italian loafers in the closet when inclement weather threatens and go for these solid and waterproof leather wingtips. They still boast loads of polish while offering a tough rubber outsole that absorbs the shock of sprinting through downpours in the concrete jungle.
The best assortment of dress shoes for anyone's closet includes a pair that you never have to think twice about. These cap-toe derbies are always appropriate.
The OG loafer, Bass Weejuns have been around since 1936, and its classic penny loafer style still looks great today. Their craftsman-like construction can hold up even after years of wear, and at under $160, it provides incredible value. An easy addition to your weekday uniform.
Read more: Best Loafers for Men
If your shoe collection is set with a black and brown pair, you can look to expanding what dress shoe actually means to you. Getting a sleek pair of boots can work for the right, less formal occasion.
Read more: Best Chelsea Boots for Men
Taft knows a thing or two about quality and comfort. With impeccable attention to detail, everything from the stitched construction, waxed laces and lavender-scented sole makes this pair extra special, oozing luxury upon unboxing. Details are what makes these shoes of excellent quality and long lasting. Once Taft hooks you as a customer, you'll keep coming back, excited to spend the $200 and change. Get ready to attract compliments, because this pair will turn heads for an elevated your pants-to-shoe-ratio.
Read more: Best Dress Sneakers
Chukkas were a staple among World War II soldiers and 20th century polo players. Now they're a menswear essential since they're durable, easy to slip on, and looks great with just about any business casual outfit. These hand-made Chukkas have a soft allow that won't mess with your pant hem, and are also eco-friendly.
Read more: Best Dress Boots for Men
High-quality leather can make formal shoes extra expensive, but these faux patent leather stunners from Calvin Klein have the same stylish appeal for a price that won’t break the bank. Plus, the grosgrain-detail is a nice touch.
Read more: Best Tuxedo Shoes
Considered to be a staple in every man's shoe wardrobe, lace-up shoes are the cornerstone of dress shoes thanks to their timeless appeal and everyday wearability. Plus, these Vionic dress shoes are made with a super stable sole that helps prevent overpronation.
The seriously soft interior and snug fit make these sophisticated loafers a top choice for wearing a cropped pant look sans socks.
The cap-toe is a sleek, timeless option to have in your dress shoe repertoire. This comfortable pair of Clarks combines the classic shape with its own signature suede, making it a great summertime dress shoe.
You can never go wrong with any Allen Edmond shoe, but this wingtip oxford is especially solid. It is a timeless shape that will last you years.
Derby shoes have an open lacing system in form of two quarters that are sewn at the top of the shoe (rather thana being sewn under or into the shoe). And while there are a ton of derby options, Dr. Martens in particular has a thick sole, making them feel a little more stylish than old-school.
Read more: Best Men's Clothing Brands
Want something even more dressy? The shine in this Ted Magnanni oxford gives the standard shoe a refined, sleek update.
Kizik’s are known for two things. The first is their “no break in period.” You’ll find lived-in comfort straight out of the box with Rabbit Foam outsoles that cushion your steps. More impressively, they are known for their accessibility and acting like a slip on. Kiziks use HandsFree technology that intentionally allows space for you to slip these on and off without ever bending down, laces tied and all. It's hard to believe this technology actually works until you experience how easy it is to slip them on and off ten times over. We're hooked. Other standout features are the genuine, full-grain leather, rubber traction pods for a grippy tread, and a roomy toe box that will never cram.
These perforated wingtips are a classically formal shoe. They are a little bit old-school but purposeful. These Allen Edmonds belong with a navy suit.
When it comes to those dress shoes that feel like sneakers, loafers tend to lean on the comfier side. You can also have more fun with them, as dressy loafers come in a variety of textures (velvet, studded, embroidered etc.) that are still suitable for formal settings.
Because dress shoes are such a timeless concept, it only takes a bit of futzing with the details to get something new. M.Gemi's loafer has a little leather twist on the front, making them special but not informal.
Look no further for the perfect work shoe. Cole Haan makes a dress shoe you can wear at your standing desk and never feel pain. Credit goes to a functional outsole that emphasizes heel and midfoot support, a padded tongue and sock lining.