Fashionista help

Last week when flying back from Philadelphia I noticed that one of the flight attendants was wearing a red hat. It was strange, because here we were on a plane and all of her hair was tucked up under this admittedly cute, but strangely inappropriate hat. It made me think how often seeing friends wearing hats had left me with this feeling that they just were trying far too hard. I'm not talking about baseball caps on a warm day or knit hats in Boston in the winter--but stylized hats intended to be an style accessory rather than a necessity.

And yet, I just saw this hat on Banana Republic's website and I am instantly in love. I'm not sure that I'd ever need to wear such a hat since Atlanta rarely gets cold enough for gloves, let alone head coverings. But I *am* going to Boston and New York next month, I am telling myself. And yes, the hat is $150 and that is crazy. But it's so cute!

But, here's the important question. Would I, by wearing this, be one of those people who's trying too hard? Be honest, don't worry about offending me and then seeing me looking like a doofus wearing it anyway in a few months. I have made no decisions yet, but I need fresh perspective.

Here is the hat in question: