Men's Dress Shoe Fit Guide
You're spending good money—they should look and feel great.
You may have stopped growing, but feet can continue to grow slightly over the years. Unless you have your own Brannock device (yes—that's what those measuring trays are called!), go to the shoe department to keep track of your size. It's important to measure both feet; your feet may be different sizes, and you should fit your shoes to the larger foot.
Because tube socks with dress shoes will never, ever be a thing, wear thin dress socks to try on shoes for a more accurate fit assessment.
You've most likely heard the (true) adage that you should be able to pinch a half inch between your toe and the front of your shoe. Take it a step further and test the back of the shoe by sliding your index finger between your heel and the end of the shoe. If your finger won't fit at all, go up a half size; if it slides in too easily, go down a half size.
Feet tend to swell as the day goes on, so try on shoes in the late afternoon or evening to avoid dealing with pinched toes.
Not all dress shoes are created equally. Certain styles suit certain types of feet more comfortably, and there may be slight differences in some brands' sizing. Take the time to try on several styles in several sizes to find the best shoe for your feet—it's worth it.