I'm with Charlie, Mark. I don't think eras or style came into play there as much as just putting the ensemble together as he saw it. Plus, no matter what, he was emulating you, and that should be flattering. Sent directly from my mind to yours.
So is his name "Open Road?" "Stetsonian?" "Stratoliner?" Now I'm curious. Sent directly from my mind to yours.
As a former Boy Scout and Explorer Scout (which is where I learned most every vice) his name is obviously "Playboy".
In the real world, I'll get a lot of compliments from the older people, and younger people just don't care. On the internet, it's a bit more complicated. "Fedora" has become a bad word on the internet, as it's become shorthand for the caricature of the overweight guy with cargo shorts, T-shirt, hat from the 40s, etiquette from the 1600s, who's a passive aggressive condescending asshole to pretty much everybody. It's unfortunate, because in large parts of the internet, see a hat, and this is the image you're conjuring up. On style forums, the reaction may be a little more justified. There's a frequent cringe pic of a guy who has poor fitting casual clothes who throws on a cheap fedora, in order to make himself look "classy." It's one thing to like hats and not care about the rest of the outfit, but if you're posting on a style forum, you're going to get advice on the outfit as a whole, so there were some strong negative reactions. It came up so frequently a few years back, when trilbies had a resurgence, there's still a pretty strong knee-jerk reaction.
Around some corners of the intertubes, it is seen as the overweight loser who white knights women, etc. But I think it's a pretty specialized niche. The folks who are passing such judgment are a pretty parochial set. And smell like stale Cheetos.
Whenever I wear a hat, it is usually of the newsboy variety. When I wear it to and from work, my employees always laugh and say "I didn't know you were Irish!" Granted, all of my employees are under twenty-one, so anything that's not a short brimmed pinstripe fedora is seen as odd. I wish I could pull off a Bogey, but alas, I am far too short and it just looks ridiculous on me.
Well, that's just about my height. Every time I try on one of those hats, it just doesn't look right. My ex-wife always use to say that it was just too big for my head. Maybe that's why she's now an ex! I've always been a sucker for that hat style and every time I go into the hat shop downtown I spend lots of time oggling them.
lots of folks ... most actually ... feel that way when first wearing hats with a larger brim or higher crown ... it is simply a matter of getting used to it I bet you look great
As moon pointed out, it's a matter of getting used to wearing a fedora. It doesn't look right because it's not what you're used to seeing in the mirror. When I started wearing fedoras ~10 years ago, I thought they looked pretty odd on me, too. Clearly, I got over that.