How Do You Find a … Hat?

This is pathetic, but I’ve never owned a hat. Please help me! I want one like the hat pictured, I think, but I don’t want it to mess up my hair (although that seems unavoidable and is also why I’ve never owned a hat in the first place). But so many of you wear hats all the time and look great. How do you do this?

What are the good, normal hats these days? Is this a ridiculous question? Does shearling give you less static than fake fur? And what’s more important, staying warm or having people think of you as someone with an average-sized head (when those two things are mutually exclusive)?