Any period of history can involve outrageous headgear. Even things we consider classy can change in a heartbeat. Fedoras used to be cool. Now they're weird and neckbeard-y.
Fedoras are still cool... if worn with a nice suit by a well-groomed person.
Fedoras worn with undershirts and untailored clothes were never cool in the first place.
I don't care if it looks cool, because it keeps my glasses dry in the rain, and the sun out of my face the rest of the time. If I want to be fashionable, I can wear something else, but mostly I just want to be comfortable.
I have this one: http://www.tilley.com/us_en/men/hats/ltm6-airflor.html
Owner's manual is worth a read, if you're unfamiliar: http://www.tilley.com/media/pdf/Tilley-Owners-Manual-EN.pdf
It's a bit more expensive than what I already have, but it looks like they have a lifetime replacement guarantee and a 2-year insurance policy against loss. All other things being equal, I'd rather pay less up front and take greater care with what I bought.
[0] http://www.tilley.com/us_en/men/hats/warm-weather/tilley-wan...