Wear many hats
Where did the phrase "wear many hats" or "wear a lot of different hats" come from?
I don't think it has a single place of origin. I think it comes from a time (not long ago) when everyone wore hats, and many of those hats were specific to a given trade, official position or function. So someone who had several roles would have several hats and would wear the appropriate one for the occasion. E.g. if a man who was an admiral, a Lord Lieutenant of a county and Chancellor of a university - each of which
has an impressive ceremonial hat - was going to an official function, the question "which hat will you be wearing?" would mean "in which capacity will you be attending?". And in theory (only in theory) if he was attending in all three capacities he ought to wear all three hats.