Just my two cents:
Wearing a hat like that takes confidence, especially if you're younger (say under 50), otherwise the hat wears you. People will notice the hat for all the wrong reasons if you don't own the look.
My rule of thumb when trying new items of clothing is that I need to "feel it" the moment I see myself in the mirror. If not, I don't go through with it. Of course, that doesn't mean it can't be tried again at a later time, as one's confidence need not be static. Given time, one may certainly "feel" an item that one could never even have imagined wearing previously.
If you can feel and own it right now, more power to you, as hats are badass.