From 94-96 it was a ratty old Sox hat (brown/black with the red B on the front)
Then I got my Soundgarden Superunknown hat (had an eblem that looked like the Superman logo, except with a question mark in it instead of an S). That one I alternated with my Curious George had that some scoundrel stole when I was at a Fugazi concert in 98.
To replace the Curious George hat (and since I'd retired the Superunknown hat due to extreme wear) I had a brown Cab hat that just had an embroidered red dragon on a brown hat.
That lasted until 2001, when I got a black hat with a red and yellow dragon on it. The next year I got a black hat with a puffed-out looking Superman logo. Puppies ate both of these hats 🙁
So as of right now I have a grey hat with an embroidered alien on it, and a black fitted Moe's Tavern hat. I rarely wear a hat any more now that my hair is long enough, though.