I can top anything anyone has listed so far. I was getting ready for the hiring convention. I did not own a suit and had not owned one for years. I can give you details about how that happens but it's not so important. I could afford one but just did not ever need one.
I took off to the local department store to find a "good suit" for my AALS interviews. I knew nothing about conservative as opposed to sporty or anything else. I had never heard of Brooks Brothers. It's a class thing. So what a wonderful suit I found. Double vents, wide lapels and something going on with the legs of the trousers. I am not sure what. YES! I had bought the pinky ring of suits. I would have probably worn a real pinky ring like my uncles but I could not afford that. To top off my fashion statement, at the convention, I wore a tee shirt under my dress shirt. It had a message that could be read right through the dress shirt. I did not realize it at the time having no need to check myself out in the mirror. I knew I looked good.
So, off I go to the convention. When I see my old law profs they do not really seem like the want to talk. In fact, it's almost like they do not want to be seen with me even though they wrote wonderful letters on my behalf. The interviews go OK but with 30 interviews I get only two callbacks -- oddly, one from a top 15 school and one from a below 50 school.
Flying back home I run into a prof of mine on the same flight. We are the only two people from our school on the flight. He does not want to sit together and keeps looking around as I attempted to engage him in conversation while waiting in line.
I got a job and wore the suit for years to all faculty social events. There was always a hush when I entered the festivities. Then one evening at a very posh affair one of my colleagues got a little loaded and said "Just keep wearing that suit and eventually it will be appropriate."
Huh? I was stunned. Was it possible I was not the coolest dressed guy. I went home and began looking on the internet and entered "business suit" which led me to Dress for Success and I realized that I had probably been laughed at for years.
But how was I to know? No mentors, no professionals in my family. And, evidently, not very observant.
So, can someone top that?