The Pimp Hat Story - Chapter 1

I have a hat party tomorrow--which means I need a hat.

Two years ago I would have worn a baseball hat or something else blandly insignificant. Today though, I went to the store and bought a bright red velvet pimp hat. I kid you not, the tag said “pimp hat.” It was, by any measure, the brightest and loudest hat on the shelf. And at $6.98, how could I say “no”?

Here's the hat.

Now, instead of worrying about the hat and will I feel comfortable, I’m worried what to wear WITH the hat. Do I dress up to compliment the hat or do I let the hat do all the talking and dress down? Would it be “incongruent” to wear the bland jeans and a black shirt with a big hat? Or should I just “pimp up” everything and go for the whole package? My life is soooo difficult.