Each other.
Seriously though, your socks should match your pants. I have heard people argue that a person’s socks should match their shoes, but as I’ve written in previous columns, I suspect this obstinacy derives from the wild variations in men’s shoe colours — from really black to plain black. Black shoes, black socks and a black suit present no fashion obstacles, but problems arise if you were to wear brown shoes or chestnut shoes with a navy blue suit. If you matched your socks to your shoes in those situations, it would make your dress shoes look more like dress boots.
Therefore, as a general rule, socks should match the pants. If they match the shoes by pure coincidence (or lack of fashion creativity) then you’re safe, and arguments to the contrary are moot.
With that general rule in mind, deviations are to be expected, and are indeed welcomed. Matching the socks to an accessory is a creative way to add a bit of style to mundane business attire. Matching the socks to your tie or your pocket square are good examples. Some people suggest that matching the socks to your cuff links or pen is also acceptable. In my view, these items are less perceptible than ties or pocket squares, and the overall effect might be lost. But, to each his own.
In closing, I would also like to insist that “socks” means dress socks. Not athletic socks. Seriously. Just because you escape for two hours at lunch to play a game of squash — while your co-workers are busy at their desks — does not excuse the need to wear dress socks with business attire. Ever.
Emir Aly Crowne is a Law Professor at the University of Windsor, Faculty of Law. He once wore dress socks to play squash.