There are a few accessories that every man should own- a nice suit, a well-fitting pair of jeans, a cool winter coat, and comfortable dress shoes. Yes, fellas, dress shoes are a must! Your lifestyle may not demand it, and dress shoes are one of those items that you don’t wear every day. But when the time comes to wear them to the wedding for example there is no alternative. 

Do you want to know what else is a must? Buying dress shoes before you actually need to wear them. Attempting to find an emergency pair of comfortable dress shoes before a big event is not smart shopping. You may get stuck with a crappy pair that you’re never going to wear ever again. Shopping for comfortable dress shoes in advance lets you avoid the stress that comes with panic shopping.

Good dress shoes don’t have to be extravagant or complicated, either. The key features that you should look for in comfortable dress shoes include:

  • Breathable Materials: Fabric such as leather and some synthetics allow your feet to breathe, which prevents blistering and reduces sweat.
  • Arch Support: People have different arch heights in their feet. You’ll need to find the right arch support that ensures all-day comfort for your feet. Too much can cause bruising, and too little may result in overpronation.
  • Cushioning: Cushioning tightens the feet and lessens the pressure on its contours.
  • Stability: Too much cushion can affect your gait. A precise balance will ensure you walk properly and avoid any discomfort from your ankles.
  • Ankle Grip: Ankle grip ensures that the foot sits correctly and securely in the shoe. This prevents the growth of blisters and reduces rubbing.

Most Comfortable Dress Shoes for Men

Comfortable Dress Shoes for Men

Wolf & Shepherd Closer Cap Toe

Wolf & Shepherd is a high-end shoe brand that designs some of the world’s most luxurious and comfortable dress shoes. By adhering to traditional styles and calfskin leather uppers, the Closer Cap Toe may look like any other Oxford shoe. However, its features include memory foam cushioning, EVA heels, lightweight leather soles, and engineering support, guaranteeing all-day comfort. Overall, Wolf & Shepherd are some of the most comfortable dress shoes out there. 

Ace Marks Vincent 

If you’re looking for a more sociable style, Ace Mark’s Italian-made Vincent is a great selection. Thanks to a Blake Flex construction, they offer enhanced flexibility and the most comfort. Similarly to the Closer Cap Toe, they’re made from flexible calfskin leather, which molds to the wearer’s feet after a few wears. Blending flawless style with traditional Italian craftsmanship, this dress show is certainly worth the investment. The best part? There are plenty of additional colorways available through their website mentioned above.

Wolf & Shepherd Breakaway Boot 

Another excellent piece by Wolf & Shepherd, the Breakaway Boot, is a newer introduction following the brand’s success. The Breakaway Boot includes all of Wolf & Shepherd’s usual features, precision design, and convenient added ankle support.  Although this boot is a great business casual option, the cap toe design means that you can also wear them formally. Rock them with jeans and then complete the outfit with a blazer.

Rockport DresSports Business 2 

Rockport’s DresSports Business 2 offers an affordable collection of professional dress shoes. If you don’t have the budget for Wolf & Shepherd, they’re a great alternative. Their truTech technology provides superior shock absorption while the cushioned insole ensures the necessary comfort required for all-day wear. We absolutely love the brogue in cognac, but that’s just us. There’s a wide variety of styles available on their website.

Beckett Simonon Lopez

Although chukka boots are usually very casual, Beckett Simonon has successfully redefined the style to offer a superior and more elegant aesthetic. The result is the Lopez, a low ankle-length boot crafted from Argentinian full-grain calfskin leather. Inspired by the boot’s First World War heritage, it doesn’t trade off style for functionality. The Lopez features a sleek and comfortable vachette lining while the rubber soles provide adequate shock absorption.

Ugg Dagmann

Most of us associate Ugg with big fur ankle-high slippers for women. However, the brand offers so much more, especially for men. Today, the brand offers an extensive selection of shoes and boots for both women and men. One of these boots is the stylish chukka boots. Not only do they look nice but they perform quite well as comfortable dress shoes. The boots are designed with the brand’s exclusive enerG Comfort System, which provides built-in arch support in the form of an added layer of open-cell PU foam. If you’re looking for a formal boot to wear to work every day, the black pair is your best bet. 

Mephisto Cap Vert

A renowned brand for designing comfortable shoes, Mephisto’s wares are not always very attractive and usually pricey. While the Cap-Vert penny loafer is indeed expensive, it’s a surprisingly chic option. The interior features a smooth leather lining with an Air-Relax cushioned insole that provides added breathability. Meanwhile, the padded tongue helps reduce pressure points guaranteeing the utmost comfort. All of this is wrapped by a traditional penny loafer style with a classic moccasin toe finish. If you’re looking for a high-end business professional dress shoe, the Cap-Vert is worth considering.


Now that you know where to get the most comfortable men’s dress shoes, you can read some of our other related guides to compliment your outfit: