Gadol, maybe – and I – are confused because we are throwback to the previous generation! Not as far as Rishonim, but maybe 100+ years.
So – for us – wearing a black hat means dressing like a Talmid Chacham, Slobodka Rosh Yeshiva, etc – and the requirement is to behave accordingly, which is a tall order, and we both humbly do not pretend.
for the current kids, when the hats are in fashion for several generation, they are dressing like their high school Rebbe, their older brothers, and customers at Lakewood Pizza+. So, they legitimately strive to that level and do not understand our kvetching.