Hat’s always ruin my hair.
How do you deal with that?
Keep it long, keep it loose, and shake it out when the hat comes off.
Back in the day, wimmins had their hair styled to fit under hats. No woman of “society” would be seen in public without a hat, especially at a “function.” So they had hair styles that would fit under the hats and still look neat when the hats came off.
Which explains why wimmins of the ‘20’s to early ‘50’s always looked like they had “hat hair.” They DID! LOL!