I have sold a lot of shoes to a lot of guys throughout my career, not only to men purchasing shoes from my own brand but also selling all types of shoes at Nordstrom. In that time, one of the things that baffled me most was guys coming to try dress shoes with thick athletic socks and insisting that it would be fine. Even after telling them that doing so would result in a half-size difference in fit, they continued to insist that it would be fine.

Although slightly annoying (when I sold shoes at Nordstrom on commission), it was more funny when they came back with shoes that they felt were now too big after trying them with proper socks. The annoying part was when they wanted to return them in order to not admit their error, but thankfully, most just wanted to exchange them for at least a half size down.

I always felt, ‘Should this not be common sense?’ The difference between a thin wool sock to a thin cotton one can be the difference between a slightly loose shoe to a well-fitting one. Socks matter, and the thicker they are, the less accurate fit you will get for trying on a brand-new shoe. Because if you won’t wear the socks you are trying the shoes on with, you are doing yourself a disservice. Dress shoes are not meant to be worn with athletic socks.

Now, of course, this is not to take into account people who like to wear heavy socks with their dress shoes. That of course, is a preference and perfectly fine if that is ‘how you wear your dress shoes,’ but this is more about the sense to know that when you typically wear dress shoes with thin socks, and then come to the store with athletic socks trying to find a pair of well-fitting shoes, that you are better off doing so barefoot than with your thick athletic socks.

Don’t try to buy well-fitting shoes on a whim. Go prepared. Or at least, do barefoot. But NEVER wear athletic socks to try on dress shoes if you intend to wear them with thin dress socks in the future. Or buy half a size down, as inevitably that will be the size you need!

Here is a simple rule to live by: A dress shoe that feels comfortable with an athletic sock will ALWAYS be too big.

—Justin FitzPatrick, The Shoe Snob

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