During the short amount of time I took the train/walked to work. I wore sneakers to get to work and then changed into my heels (or boots) once I got to my desk. I vote not old - just smart!
Who's staring at you? (Either way, I bet it's because you look hot!)
I wear flats and switch to heels. I don't want to ruin my fancy nice heels on these terrible sidewalks. It would also take me 3 times longer if I walked in them to work. I'm all about walking distances in comfort.