A Crazy Hat

The other day I was walking around Bloomies when I spotted a stack of random hats on sale. Being on sale the selection obviously wasn't that stellar. It was all really rather old ladylike and odd. But inspired by HG's hat post, I decided to play around and try them on anyway- just to see how outrageous I'd look.
Surprisingly during the process, I got attached to one hat in particular: a black felt wide rimmed hat with a simple black patent belt wrapped around it with a discrete bow (above). It was just so ladylike and simple. And at that moment, I thought it actually looked quite good on me!
It reminded me of the women in those (60s?) posters wearing a big black hat, looking really elegant and ladylike (a bit like the poster above). And I'm nothing if not a sucker for ladylike looking things. Encouraged by the saleslady who claimed she got one too and by the fact that after an additional 50% off, it was only $5, I bought it and wore it for the rest of the day just to prove my friend, who told me that I'd never wear such a crazy hat, wrong. A good thing too, since I ended up going to a golfing range that day and it proved to be a very good defense against the sun. I thought it was really cool and ladylike. The rest of my friends hated it though and thought I looked witch like.
On the other hand though, it gives me hat hair, so I'd look really weird going indoors with it, but since it is felt, I can't very well wear it to the beach. So where would I wear it to? And the other problem is what would I WEAR it with? If I wear it with jeans and tank top, I'd look like I just picked it up off the sales rack to try on (which I guess I did). But if I were it with something equally somber and ladylike to match the hat, I'd look like I was going to a funeral. I considered wearing it with my American Apparel black dress (above shown in Raspberry), because it is simple but the cutting is still rather casual and young....... but the too black thing comes to mind. Maybe I should just get that dress in this Raspberry color.........or maybe some accessories? Decorate the hat with a brooch or a colored bow? Suggestions on how to carry this off?

I know, most of you probably think it's a really crazy old lady hat and cannot fathom why I'd buy it in the first place. I guess I just cannot resist a bargain (it used to be $70). Maybe I'll just save it for Halloween! :P

Image Source: Hat-a-tude and American Apparel