I used to usually wear the straw boater since there really aren't any hairstyles that match mine, and when I wear the hat, it covers up the fringe of my usual hair style in New Leaf so it looks more like me. c: But now I wear the Santa hat, to get into the festive mood~! ///
I always wear a hat. I just like them. I like wearing the straw hat from the island or the purple baseball cap, but for winter, I wear the purple knit hat. My favorite color is purple after all.
It always depends on the outfit I have my character wearing. Right now, for example, my character isn't wearing a hat, and hasn't been for a few weeks. Before that though, I had my character wearing a few different hats.
If I had to pick just one though, I'd lean more towards not wearing them.
My character looks strange without a hat. Recently I was wearing the Flamenco hat, but then the little crown popped up in able sisters so she bought it. (oh and then I got one from my Secret Santa. THANKS!!)