OK I was definitely looking at the first page when I commented this... that's embarrassing. Either way, I still say hit. Edgy, different, but still under control. I like anything with a little undertone of strange.
With that being said, if you can rock the hell out of it, wear it.
I want to say miss... but I have to say hit, I love that laid back look. However, take off the hat and weird ribbon and replace it with some other accessories I would probably be more on board, I agree with the whole 'trying too hard'.