It all began, for me, in the army... having to wear a cap. After my discharge I continued.... but caps were standard for Farmers anyway... whether I had been in the Army or not.
That continued for the next 30 years or so... mostly Ram caps but also various 'Ag' related caps, many. Then there came a day - - - - - - -
I was looking at photos of my Dad's family, the old timers, and all of them in Fedora's. They looked dapper... I was impressed. Thus: Bought my first fedora. Also, I think a Fedora is mandatory if you're Italian.
Today I have many hats.. mostly Fedora's but also a couple Bowlers, Homburgs - couple 'cowboy hats', some what I call "Indiana Jones Hats"... and I have several versions of each... for example I have a Felt Fedora, a Straw Fedora, a Crushable Fedora.... I have a Beaver Cowboy Hat and also a straw Cowboy hat.
Most days I wear a straw Indiana Jones hat... very comfortable, easy to care for because you don't have too... the more wear and tear it exhibits the better. I don't wear caps very often at all these days... very rarely.
I do wear several different "Bucket Hats". Extremely comfortable and you can bend and mold them as needed.
Several years ago i was very surprised to learn that Stetson mades a LOT more than just cowboy hats... I have a Stetson Fedora, a Stetson Bowler, and a Stetson Indiana Jones hat... some others as well. Simply put: you can't go wrong with a Stetson.
The crown jewel of my hat collection is an Italian Fedora that set me back an arm, a leg, and my left testicle. Not sure it was worth a testicle BUT... it's a damn nice hat. - JamesJM