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I sometimes wonder the same thing. Ever watch an old movie or see a clip from an old ballgame? Everyone is wearing a hat, and most are wearing a tie, even at a baseball game or movie. While I'm not a big fan of ties, I think hats are cool...fedoras, Panama hats, pork-pie, etc., though I rarely wear a hat, with the exception of being in uniform when I have to while outdoors.
I have a few authentic hand made Panama hats I got from Monte Cristi Ecuador but I never wear them. Once in a while I wear a baseball cap, but not often. It also makes me crazy to see someone in a restaurant with their hat on. I'm not talking about a taco stand or McDonald's, but a real restaurant.
I wouldn't even know where to go to buy a hat. Yes, a haberdashery, I know this. But I wouldn't know where to find one.
I did buy what I call a "driving hat", Short brim, flat and rouind--it had a bit of a pattern to it--but I don't know what happened to it.I think my size is 7-1/4.
My woolen watch cap doesn't really count. I only wear it when it's pretty cold out.
When did wearing a fedora go out of style? Seems like in the '30s and '40s, a man wasn't considered dressed for public if he didn't put on his fedora. He tipped it to the ladies, took it off indoors, or if the flag came by.
Nowadays, IF a man wears a hat, it's generally a baseball-style cap...and he feels no compulsion to tip it to a lady, or take it off when entering a building. You'll even see men with ball caps on as the flag goes by them.
Now, I'm willing to admit that I've been guilty of this myself, where it comes to ball caps (except for the thing about the flag)--but when exactly did the fedora go out of style?
Nah. My 17 year old son wears fedoras and is perfectly comfortable. And the girls love it. The problem is that so many people are SHEEP and wear only what everyone wears. Get a little individuality and make your own style.
A Fedora hat on a man is totally sexy! It's the finishing touch that just screams hot! It's a shame more men don't wear them. But I'm also old fashioned; if you wear it, you should follow the rules of etiquette--no need to be sloppy when showing style!
With all the women liking hats, I wonder if that's the attraction to a man in a military uniform.
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The problem is that so many people are SHEEP and wear only what everyone wears. Get a little individuality and make your own style. 
