Just answer this simple question; are you a Baseball player?
Personally, I like baseball hats. Wore 'em with hair, wear 'em without - although when it's warm I'm definitely more comfotable lid-free now (the shaved head does get pretty sweaty and uncomfotable under a hat). They do come in handy for blocking out the sun, though.
As long as you're not using them to hide your hair loss, or your sly noggin, I say wear one if you feel like it.
I rarely wear head gear unless extremely cold or attending a PENN STATE GAME
I've got many...
I know I'm going to get it with this admission...but to coordinate with different outfits...
And as I commented in similar posts, I wear it backwards...
On reading this thread I realized that, since slithering over to the sly side recently, I have not worn one of my usual caps. Not once. Even when I probably should have on a couple of pretty hot days here. I used to wear one of a cool collection of caps daily. I know I put one on, briefly, once or twice. Then promptly removed it before venturing out. Not sure whether a cap was just not comfortable any more, or if I just preferred the great liberating feeling of "exposing" my dome. Probably a bit of both.