I only wear hats to make some kind of statement or to wear as a costume. I have a pretty black fur Russian hat with a Soviet Russia hat pin on the front and I have several sombreros and I have a couple Mickey Mouse ears from Disneyland and --though these aren't really hats they still make a big statement-- loads of headbands with big flowers and feathers and crazy things on them.
I only wear a hat when I feel like having some fun.