>>83018715 (OP)
>when does this happen?
When you get something that stands out and isn't trashy. I like certain kind of hats that were popular around century ago. These days barely anyone wears them, it's either people who recreate historical stuff or old people, and even old people tend to wear a bit different "old people's hat". When I asked on the internet how anons like it because I'm considering getting one, I was told it'd look pretentious and cringeworthy, like fedora wearing militiant atheists in 2010s, and like old man. I decided to buy it anyway and so far irl I've only got compliments for it. Only person who doesn't like it is my mother because she's massive conformist who values what other think above own family.
Now I have 2 such hats: one woolen, much fancier looking, for winter, and one light, made of just linen, for warmer seasons. You aren't going to get complimented on looking like everybody else.
>does it ever happen?
Yes.