banananutmuffin: LOL. My DH doesn't normally like when I wear heels because he's a short guy - only 5'8" so mostly I wear 'kitten heels' or flats. Wouldn't want to bruise his ego. And it's rare for him to compliment me on my clothing after 20 years together. So when he said that the shorts with the tee shirt and heels were a look that was 'very becoming' - well, let's just say I had a sh**-eating grin on my face for at least two whole days.
I say GO FOR IT!!! My Mom is 60, and I argue with her every time we go shopping. She thinks she can't wear anything that is mid-thigh, but I'm always trying to tell her that she looks great, and should own it. It NEVER looks inappropriate!