Personally, I find "hat" to be an incredibly hilarious word. Hat. Haaaat.
Anyway, that's not my point. My point is that you should buy one and wear it. It's really hard at first, as not many people wear hats. You will feel very obvious and maybe like you have a giant squirrel perched on your noggin, judging by the way people will look at it while talking to you or passing by you. But really it's because you look totally great and they are trying to figure out how to incorporate a hat into their bag of accessory tricks.
Just like trying out a different hairstyle, not every day is a winner. And that's ok. Carrying off a hat requires confidence that you dont even know you have, but once you have it, you will find yourself aching to stretch even further out of your comfort zone. Do you want to be blandly pretty or daringly gorgeous (and sometimes a little insane)?
First, find a hat shop. Even a place like mall staple Lids has a pretty good Kangol selection (and you cant go wrong with Kangol, man). Depending on the season, Nordstrom seems to have a few carefully edited selections. People have some passionate hate for fedoras, but trust me, they're a pretty good gateway. It takes a little time to find the correct brim size for your face and body, but it's a hat style in which most people look good. Play around with tucking your hair inside (with some wisps sticking out to keep it feminine) or keeping your hair down. Fedoras, I can wear either way, but a newsboy (another great gateway) I only like with my hair tucked in, just a few pieces of hair hanging down. The benin (second photo) - that's a more advanced style to pull off (but SOOO. FUN. I get a million compliments in it and it just elevates any outfit. It took me 5 or 6 years of never ending scouring of ebay to find it until I finally found an Etsy girl to make me one custom (highly recommended, when you're ready). I think I need to order another, but I may wait for Fall so I can get a nice brown wool (hopefully GirlFauxPas will be back from vacation by then!). I like a little structure, but a lot of people feel more comfortable with a slouchier hat like a beanie or a beret. I have a small head so these look like the hat is trying to eat me. I'm not sure if I'm a fan of it on other people, either. I love some Rachel Zoe, but I do not love her taste in hats. I feel she could look soooo. much. prettier. (Of course, now that I'm searching google images, she's in all fedoras and looks GORGEOUS. Perhaps, she was just really into beanies during filming?) But there you go, she feels confident, so I'm glad she wears it. It's definitely memorable and completely her. In my book, that's better than pretty.