Most Helpful Guy
The problem is not with the fedora itself. The fedora used to be associated with class and style. The problem is with the type of person that started wearing the fedora... changing what it was associated with. When a lot of people that are NOT associated with class and style started wearing the fedora, it started to become associated with them instead. A really stylish person can still pull it off and look good, but the generalized 'vibe' of the thing has been completely changed in the last 8 years or so.
When someone said 'fedora' in the past, you got images of sharp dressed guys in suits with a bit of class and some style. When someone says 'fedora' now, you get images of an overweight guy with bad skin and greasy hair in a t-shirt and jeans. And that just doesn't carry the same level of sophistication.4
Most Helpful Girl
They can sometimes seem pretentious. I like them though.1