When in doubt, turn to Reddit. A curious man submitted an inquiry to the sub-Reddit "Ask Women," in which he asked the lady Redditors what they actually thought about fedoras, and the personality that often comes or is at least associated with it.
I'm talking about a guy that wears a fedora (or maybe any other hat) and does things like tipping it to you, says things like "m'lady", stands up when you enter the room or exit the table, kisses your hand, etc.
Assuming the guy is fit, practices basic hygiene, and doesn't have a neckbeard...wouldn't you find this sort of thing charming/cute/sweet in an old-fashioned sense (especially when nobody does anything like this these days)? If not, why not? Is it just that most women don't like it, but there's a small sub-set that do like it?
The inquiry got over 500 comments, and the basic answer is no, women do not like the "fedora persona." So if you're that asshole reading up on pick-up artist techniques while doffing your cap and saying condescending things like "m'lady," according to the majority of women who weighed in on this sub-Reddit, you should stop. And even if you're not, please remove and burn that fedora, because these are the assumptions people are making about you because of your hat choice.
Not convinced? Here are some choice responses:
And there a lot, lot more.