Shopping for mens shoes should always focus on fit and comfort first, and finding a fashionable, stylish brand second. Quality shoemakers know this and offer a wide range of comfortable footwear options. Brands that are merely fashionable are not going to serve you well if they don't fit right.
Shopping for shoes that are comfortable and also look good is easier than ever. In order to get a proper fit, you should shop for shoes later in the day, when your feet are larger, and be sure that the brands you try on aren't too tight. You should be able to wiggle your toes. You shouldn't hold on to the old notion of foot size - your body changes, and you really should get your feet measured each time you buy shoes. Also, make sure that you get both feet measured, as sometimes one foot is larger. The shoes should fit the larger foot comfortably.
How Do They Fit?
For the most comfortable shoes, you should try them on with the same socks that you will normally wear with the shoes. Make sure you try on both shoes, and walk around the store a bit before purchasing. Buckle or lace up the shoes as you normally would during regular wear. Make sure they fit and bend in the same places that your foot bends. Don't buy leather shoes that are too tight and expect them to stretch out and be more comfortable once they are “broken in.” They should be comfortable when you try them on and walk.
An experienced sales person in a store with a knowledgeable staff can help you find the right fit and the right styles for your needs. They will be able to steer you toward brands that offer special features for your personal fit needs, such as arch support, and proper cushioning.