the 1940's fedora is not really made anymore the ones that greasy neckbeards wear are a cheap version of a fedora called a trilby. They are completely different hats. The one Gregory Peck (god Gregory Peck is hot) is wearing in the first picture is a fedora, the one the nerdy guy is wearing in the second picture is a trilby.
There's this guy at school who wears fedoras sometimes and he looks great! It all depends on the rest of the outfit. I think if a guy wears the right things to correspond with the fedora then he'll look quite attractive
I remember seeing a youtube video of a proud fedora owner, ignorant of the fact it is now looked down upon, showing off some of the tricks he could do. The comments were all bullies making fun of it. You can't wear a fedora anymore this day and age.