Sooner or later, this subject always seems to come around:
Now I know someone probably remembers that at one time or another I said that one should not wear socks with sandals but I also said that it’s okay if the sandals are casual and the socks are the kind that are meant to be shown off — novelty or any kind of print or colorful socks. Besides, how can I be a fashion rebel if there are no fashion rules to break, so I defend and perpetuate the rule and break it at the same time. I think the “no socks with sandals” taboo probably came about because of guys wearing grubby athletic socks with sandals, which is gross, guys. Just stop that. But in spite of my bold talk about fashion rebellion I probably won’t ever go out in public like this. Or maybe I will. Who knows?
Well, I certainly don’t know. But the thing about rules, and not just fashion rules, is that sometimes you break then, sometimes you bend them, and sometimes, in the spirit of defiance, you actually follow them. (I swiped this particular bit of wisdom from Charles Goren, who would probably be amused to see it used in this context, perhaps less so to see me leading the top of nothing against three no-trump.)
As for the origin of the taboo, I blame these guys.