Welcome, Tyrone! Were you referring to the wool pullover caps or the traditional ball cap? Either way, I work outdoors (mostly) and wool hats made my head itch, mostly due to working in dust. I found out that wearing a stocking cap/wave cap underneath keeps the wool hat from making my scalp irritated. That said, a big key is to keep applying some form of lotion and washing your scalp at least twice a week to keep your head from drying out. Good luck!