1. Diane Birch, 2. Alexa Chung, 3. The Stylish Wanderer
Not everyone can pull off hats flawlessly, but when they can you can tell. I think it's about finding a hat with the perfect fit.
I personally think older, maturer men tend to pull off hats better than younger men. I think it's because they wear it with a degree of formality, as they were intended to be worn, but younger guys nowadays wear them tilted, with skinny jeans and other fashion profanities that would leave Frank Sinatra rolling in his grave. It's actual odd to see a woman wear a hat formally, so we kind of have the better end of the deal.