This while hiking, but have been considering a switch to this.

I frequently wear a flatcap.

A beanie in the fall because I look cute in it

I think it was my sons pants to make him laugh.

Does a bike helmet count? If it does, then that. Otherwise, warm beanie whenever it was last cold.

A beanie in the winter because it was cold outside

Baseball cap! Wearing it now actually. It has a mesh back and a gray front with my state’s shape on it patterned with a rainbow 🌈

Victorian style top hat

Not sure. Either my 1890s mailman cap, my medieval nasal helmet or my cowboy hat.

Head hat

wide brimmed bucket hat, for sun protection.

A Stetson straw wheat gambler hat. I have a lot of hats, but this one allows for maximum air flow.

Strawhat in the Summer

A light grey flat cap

Kangol flat cap, gray. I alternate between that and a beige flat cap with a closer fit, which is the one that got me into flat caps.