For better or for worse, I love hats. JFK killed the hat industry as he was the first President to go w/o one. The fashion of not wearing hats followed his lead. My only problem is when the Fedora is seen as a religious obligation or as a holy item. It’s a hat.
I wear my black hat when a) it’s raining or b) when it’s too sunny out. Again it’s just a hat. To those people defending hats as an obligation: would you be fine with me coming to shul in a Fez or a Top Hat?