How do you deal with it if/when you wear a hat?

Further to my thread on hats, I wonder how those of you who do wear hats, deal with whatever happens underneath - from flattening out curls to static electricity!

For the most part, I get my hair cut into a shorter ‘Bob’ style that looks good styled straight under a beanie. If the length gets too long, the ends flip up and out, and anything that gets damp (from drizzle or snow) curls and frizzes while the top remains straight. Not a good look. There’s a very specific length that works, annd any hat seems to work positively at smoothing the ‘do down - better than a flat iron.

If I want to wear my hair curly, I wear a beret, which has a looser fit and is less likely to squash the curls. Wearing a beanie with a curly ‘do gives off an evil clown vibe I try not to cultivate.

Does wearing a hat influence how you have your hair cut or styled? For those who don’t wear a hat - does your hair style factor in this decision?

PS: as a glasses wearer, I ‘get’ the extra challenge of wearing a hat whilst trying to look cute!