People don’t think some guy and his wife look like losers when he’s wearing a fedora. People think a single guy in a graphic tee with a fedora looks like a loser. Go dress sharp, the only people whose opinions of your appearance matter seem to like it when you wear one.
I shared a house with a partner during the pandemic. She was a gusher. So to save having to wash and replace her sheets all the time, she'd lay a dog blanket down any time she was having sex. And we are polyamorous, so she was having a fair amount between me and her two other partners.
I personally wear hats. A fedora is one of them. It can be hard to dress for, but I tend to underdress rather than overdo it because wearing it casually doesn't make me look like an internet meme. Helps to be a bit older, too.
The trick is what you wear with it. Yeah, if you wear it with an edgy t-shirt, cargo pants, and a trench coat people will think you're an asshole. If you instead wear it with, for example, a casual button down shirt, sturdy slacks, and in colder weather a light leather jacket, people will think you look like Indiana Jones. I know because that's how I usually dress and random people compliment me on that. As long as the outfit suits the hat, people will see it in the way you mean it.
There's no saving the Trilby hat though, there's no outfit that makes it work. Edit: I was wrong. Even the Trilby can be cool.
I wear a trilby and get compliments frequently. People tell me I look like: The Blues Brothers, Inspector Gadget, Dick Tracey, and one guy called me Inspector Clouseau.
Damn, you're right. I didn't think about the Blues Brothers, who do in fact look very cool in trilbys. I guess it just requires the right accompaniment like any hat. I apologize.
My brother has a bowler. It can look damn stylish with the right clothes, and downright silly with the wrong ones. I can't wear one though, I look silly in them no matter what I wear it with.
Whenever I hear the word 'trilby' it immediately makes me think of the song Gone to the Dogs by Squeeze because it has the line "in old overcoats and trilby hats."
I've had to stop listening to his review. Not because I don't like them, but because I'm way too impressionable with negative reviews and it turns me away from too many things. I miss it.