I used to wear a hat but never liked how it looked or felt, it was mostly habit from young age and being in yeshiva.
Wife finally told me why the heck do you wear it if you hate it?
Stopped wearing it 5 years ago and don't miss it in the least. Most people wear it just because it associates them with our community not because they like how it looks. Why should i shell out $300 plus for something i dont want in the first place..
Some enjoy it because it covers their hair-loss, but thats a whole different topic.