@Paul4747 Fedora-like hats in the early 20th century were often worn by both sexes. But it’s the men of the 1920s through the ’50s — business executives, gangsters, detectives, journalists, and the Hollywood stars who played them — who would end up creating the idea of the fedora as a distinctly masculine item.

You can pretty much blame Justin Timberlake for the comeback of the mid-2000s. Even though all he was trying to do was bring sexy back, instead he ended up bringing back the sartorial equivalent of Pepe the frog.

All three of our menswear experts agreed that the fedora, despite being a classic, holds terrible connotations. “I think the fedora has gotten the worst rap out of all of them,” says DeLeon. “If you were ever going to find a picture of what an internet troll looks like and a men’s rights activist looks like, they would definitely be in the middle.”

“If you saw a fucking dude wearing a fedora on the street, where does your mind immediately go? This dude loves to go to cocktail bars on the weekend and is an amateur mixologist and is an incel on Reddit or whatever,” says Schlossman. And despite the fact that Zaboklicki wears them himself, he says, “Even today whenever I wear one, I’m like, ‘God, I look stupid.’”
[vox.com]