My go-to cap for playing and going to the ballpark was a fitted cap I bought at Grandstand in 2000 on a hot Sunday afternoon before a Sox game in the glorious summer when New Comiskey was the funnest place on earth. The current regulation cap, then and now. It has some stains now, but it remains the most comfortable cap I have.
My go-to cap for hiking and adventure used to be a khaki cap, a former Cell giveaway, that I was given. I did a lot of hiking in it in Southeast Alaska, where it sheltered me from the rain. I lost it one day while hiking in Hawaii when a gust of wind took it into the trees downhill from me.
I do have a lot of caps from different eras and different novelties. Except for Sox games, and the Sox might come to Oakland just once a year, so I don't get to many, I don't wear caps much anymore.