Fit: Just as with any other shoe, finding the right fit is nailing that middle ground between cramped and loose. If your feet are compressed for long periods of time it can not only cause foot pain but negatively affect the rest of your body by throwing off how you naturally carry your weight. Too much room, on the other hand, and you will cause friction that results in blisters. When you try on a pair of shoes, make sure you can wiggle your toes and spread them out. Comfortable dress shoes avoid the pointed toes that looked nice on some traditional dress shoes, but are not friendly to toes. You also want to make sure your heel sits firmly against the back of the shoe as you take a few steps.
Color: To maintain a proper dress shoe look, you want to stick with the usual colors like black, brown, gray, blue, and cognac for the upper. If you’re going with suede, a lighter sandy tan color is a good choice. Soles may contain composites of various materials but they should be a uniform color, or close to. A solid black, brown, or white sole is preferable. Contrasting between the sole and upper is a good look, like a brown upper and white sole for instance. Avoid bright colors or sporty patterns that you might find on a sneaker.
Sole Material: All three layers of the sole have seen significant upgrades in comfortable dress shoes. Insoles are more comforting with modern materials like memory foam and gel pads. Midsoles are ergonomically shaped to provide arch support, heel cradling, and absorb toe pressure. Whole slippery leather outsoles have been replaced with firm gripping rubber. Whether you go for a classic heel or an athletic style flat sole, your feet are getting pampered.
Upper Material: There are plenty of comfortable dress shoes out there that have strayed too far into athletic shoe territory by ditching the leather, or at least leather-looking uppers. It is important not to lose the “dress” part of dress shoes by wearing something that looks like a fancy trainer. The best shoe makers are using softer, more accommodating leather to retain that familiar dress shoe look while enhancing comfort. The rule of thumb is: As long as the upper looks dressy, the sole can be more athletic.