Ideally, you want a hat that won't outshine you, right? At least, that's my philosophy.
A good hat will enhance your best facial features, minimize the stuff you don't like, and won't look like some kind of parade float on your head. And it all really depends on your face and more importantly—your attitude.
I often wear funky, eye-catching pieces on my head, but I make sure I never let them dominate. I'm lucky to have pretty strong facial features, so I can get away with a lot, or I use my clothes to balance the look out. I also have the right attitude—put it on and forget about it! If you're self-conscious about what you're wearing, people will sense it.
So, when choosing a hat, look at the whole picture of you and not just what you're putting on your head. Adjust the hat, adjust your attitude, walk out the door and shine.
Photo courtesy of Flickr: vinceconnare