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Thinking of buying 3 color Fedoras: Black, White, and Gray. I just think they’re interesting and cool looking hats. But I hear the old stereotype with it is it is kind of like hats worn by “Wiseguy Italians” or “Mafia Organized criminals?” Is this considered 100% true? Just wondering if I start just wearing fedoras around as a habit: Will people “associate” me with that kind of thinking? Thanks
I think you're referring to a Tribilly, the kind you'd picture a stereotypical "Neckbeard" wearing. A fedora would be what Indiana Jones wears. But to answer your question, nobody's going to think you're in organized crime, unless you're Italian, slightly overweight, and wear a suit and tie with your "fedora". So, I'd say you're good.
The last 20 years have seen the fedora drastically lose popularity. They're now associated with a meme from ages ago where an overweight man (teen?) is tipping his hat with the phrase "M'lady." written under it.
It has since become associated with neckbeards and incel culture.
Fedora hats can be thought of as you in the mafia, but they can also be thought to be cool, that's because they look cool. Besides, the classy guys wear fedoras, you can dress any way you want, but it's not for average, classless people. It's all the lie of how good you look when dressing like that makes you look trashy and weird.