score:6
"Hat hair" was a universal affliction when all men wore hats. Sometimes they don't bother to fix it up after taking off the hat, even when taking a photograph, and so you end up with photos like this:
If you look through lots of photos from that period, you can find plenty of examples of hair with the characteristic hat crease.
Given that the pocket comb was once commonly carried by men and women, I imagine that's how most people dealt with hat hair - or not at all, as in the case of the famous hat-wearer, Abraham Lincoln, who had a reputation for very messy hair.