I think the comments here indicate part of why Fedora is a thing.
 
I immediately look at this and wonder why he thought the outfit choice was a good idea, fedora being irrelevant. The colors and design looks tacky to me.

But others say that it looks alright or even good.
 
I think the differences in taste are so disparate, that one group of people generally likes this and another group generally thinks it looks silly. So you have a group of people who wear the clothes/fedora, because they thinks it looks cool…and another that laughs at the other group for thinking it looks cool.
 
You know…like high school. Bowling for Soup had a song about that, I think.

Actually, this guy is doing it quite right. It's his young face that spoils the overall effect a bit. But still.