Both. In my case for example, I have a condition called delayed sleep phase syndrome, which causes me, on average, to not even feel tired until well after midnight, and actual sleep will alude me until after 3am. This is regardless of what time I wake up btw, I could fall asleep at 3am and wake up at 5am or 2pm and I'd still be wide awake after midnight the following night.
On the other hand, I know quite a few people who can adapt their sleep schedules fairly quickly to switch from a morning person to a night owl or vice versa.
The issue is it has to fit the overall outfit. A fedora can still look really good if you have a well tailored suit to match it, while most of the things that look good with a cloak are, frankly, uncomfortable to wear everyday compared to modern clothing. This is why it's essentially only done for cosplay and larping nowadays, looking like that is fun every now and then but not so fun that you'd want to go about daily life dressed that way.