Meno – I can’t answer you since I have never worn a black hat, but I will tell you that on my friend’s daughter’s birthday when she went around the table giving brachos to everyone, she gave me a bracha that I should be very tznius and wear tights day and night.
I did not say Amen to that bracha.
But given the choice, I think wearing tights 24/7 is easier than wearing a hat 24/7.