I started wearing a flat cap around mid to late 2019
I'd been looking for a decent one for years and finally found one, so I wore it everywhere (still do)
The amount of dudes complimenting me, asking where I got it, etc. is wild. I think im Up to over 10 comments, which is insane for someone who's never gotten any in public before
I wish I could wear something like that, but it'd make me feel pretentious. Not that I think people wearing them look or come off as pretentious, but for me it'd feel that way. I couldn't pull it off anyway since my daily attire is a hoodie and jeans/joggers.
Growing up with that sort of stupid toxic masculinity no matter how dumb you realize it is... is just hard. Every fiber of your being screams to tell you no, don't stand out, suck it up, what are you some kinda of douche?
There are so many styles, patterns, and colors of caps under the very wide term of flat cap. I think the pretentious feeling is silly, and probably geographical. I have baseball hats, beanies, newsboys, whatever. It doesn't have to be your thing, just a thing you have.