Stu Rasmussen was elected mayor the first time in Silverton, Oregon dressed as a man.....but then reelected as a "women".....That makes this one really unique.....
A little side note: I was a bank manager once, long ago in this sleepy little town, hahaha....and it is a fairly conservative place! I couldn't wait to get out.
http://abcnews.go.com/GMA/story?id=6211839&page=1