Before the dawn of the Internet, all men bought their shoes in brick-and-mortar stores, where they’d try on different sizes until they found what was most comfortable. Today, many men learn about new brands online, and then scour the Internet looking for a support group of like-footed people who are 10D in Allen Edmonds and 10.5 in Converse to tell them what size they need in their new favorite brand. Some of these nuisances can be done away with if you buy directly from a store that can give you sizing advice (better still if they offer free returns). Even so, you'll need to know how to tell if your shoes actually fit you.
One telltale sign is in the eyelet tabs. These should be relatively straight, or form just a small “V.” If the spread of the “V” is too wide, then it might be a sign that your shoes are too small. If the tabs crumple on each other like tectonic plates meeting to form a mountain, the shoes are too big.
If your shoes are too small, one of the first places you’ll feel discomfort is around the ball of your foot. With the shoes on, squeeze the sides of your shoe to see if it’s too tight. It also helps to walk around a bit (obviously on carpet, so that you don’t scuff the soles) so you can see if the vamp cuts into your feet. The vamp is the area on a shoe that flexes the most when you walk. If the shoes are too small, the leather will cut into your instep, making it difficult for you to walk long distances.
Similarly, when walking, notice where the shoes are bending. If the flexing is happening too close to the end of the shoe, it’s likely that your shoes are too big. This is easiest to see on toe caps, where creasing should never go into the toe cap itself.
Of course, all leather shoes – especially those with hard bottoms – need some breaking in. Slip-ons, for example, can often have a little heel slippage at first, but that goes away after a month’s worth of wear. In the beginning, however, all shoes should feel reasonably comfortable, and not need any extra padding or inserts to fit. Start by knowing your official Brannock size, and try on shoes in the middle of the day, when your feet are most swollen. If the shoes fit well enough, they’ll break in with time and feel like they were custom made.