"I was voted "Most Likely to be Out of Dress Code" in high school, because I was always getting detention for breaking dress code. It was a pretty cool honor to have for a senior superlative, because it was about as rebellious as you could get at a Jesuit high school.
As an adult that would just get me fired if I was constantly breaking the dress code of a place that had one."
Found the kid/uncool adult!