Mostly it's the associations that have been formed with the most recent "neckbeard" clans wearing them. It's one of those cool things to hate, like Justin Beaver and the like.
There's nothing inherently wrong with fedoras. They're good head umbrellas to keep the rain off of you when walking in said falling water, and with the right geddup they can be quite stylish. It's mostly the culture associated with them nowadays combined with the fact that modern fashion isn't exactly conducive to the addition of a fedora, so wearing one becomes a clashing and specific choice rather than just a casual common one.
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