The all matching socks strategy breaks down over time. Eventually you need to buy more socks, and the new ones aren't as worn as the old ones, so you end up having to match them anyway. My solution to this is to buy a large batch of identical socks. Then when you need new ones, buy another large batch that are slightly different - e.g. grey hiking socks instead of black, or wool hiking socks that have a slightly different pattern but are still the same style. This reduces the matching problem from matching all pairs to matching into a couple different sets, which is much easier.

I've thought too much about this.