Here are my most worn hats:

CasualBox Beanie - I have two of these. Super soft and comfortable.

ShariRose - I like that you can tie this one a variety of ways.

Also, if you haven’t looked at them, I’m obsessed with my halo wig . It’s light weight, easy to care for and I just wear a hat over it. I linked to the one I have but I’ve worn it almost everyday for 5 months.

Good luck!