My boss has the extraordinary ability to let me wear what I wish, granted that it is modest and vaguely professional. "As long as they learn," is how she counters my more bisarre ideas ("Can I come dressed as a pirate? How about a Jedi Knight?"), which I think is a very healthy way to go about things. Perhaps more leaders need to be like her--willing to change, to try something new, to approach the subject from a different angle.
One particular day I came dressed in stripes from top to toe.
My black and white striped pirate pants that I bought for ten dollars in Chinatown.