Did you ever have one of those Halloweens where your costume fell way short of awesome? I sure did. I was going to be a killer robot. I had two boxes, a large one for my body, and a smaller one for my head. I cut armholes in the big one and a hole in the top, where the other box went. I painted the whole thing orange, and cut out eye holes. About fifteen minutes after leaving the house, I realized the total and devastating failure of my endeavor, and returned home a sad, orange robot disgrace. I know there are other stories out there that beg sharing, like Susan's as told to Lemondrop, among other confessions:
My brother and I dressed up as George and Martha Washington one year. (My Dad was a big history buff.) Yup, it was incredibly nerdy. And also kind of funny that I was about a foot taller than "George Washington." (pictured, above).
More terrible costume stories at their site, but since I confessed, it's your turn! What costume idea of yours turned out to be less than you'd hoped for? Link
I was still refusing when my aunt was putting make up on me and I was in this frilly pink dress, blond pigtails, knee socks and patent shoes. My cousin wore a baseball cap, a sweatshirt, jeans and sneakers. I was teased to no end at school, even by my teacher. That night I was not recognized and asked several times what I was supposed to be. My cousin was too happy to answer for me.
That was definitely regrettable and it was the last year that I went trick or treating.
Thank God the wisearse does not allow Halloween in Oz!
I knew a guy who's mom had dressed him up as Hitler and sent him to school.
I also heard a great story on This American Life about another kid who got dressed up as Hitler at school and how the teachers dealt with it.
Personally, I was always content to be a cat or a witch or a vampire. If it was black and involved makeup, that was enough for me.