Dunno if it’s true or not, but I remember reading that Picard brought being shaved bald to the mainstream. So like, folks younger than the thinning hair age would do it.
Again, can’t vouch for if it’s true or not, but if true, it would suggest it might be possible…
… that said, a cool character would probably have to wear one. And not just nameless background extras.
I mean, the easiest way would be to read the novels by publication date… I don't think there's a short cut around that.
That said, having full context is… not always worthwhile. Sometimes just knowing that something happened in the past is more enjoyable than reading it in practice.