I am not horrified by anything I wore to high school, because after 2 months at Miami Palmetto HS, I told my parents I refused to go back for my junior year. I went to a very small private school, where I could not even wear pants to school, in 1969-1971. So while my friends in Newton, MA were demonstrating on the Boston Common and generally not doing anything to please teachers and parents (who were also smoking weed and demonstrating), I was thrown backwards about 10 years. I did wear midriff tops, sans bra on the weekends, and skirts as short as I could get away with at school. I do remember "hot pants," but I don't think I work those to school. Seriously, granny dresses were in style while I was in HS and the beginning of college, so no skimpy stuff there.
I started dressing quite a bit brazenly, in the 80s, when I was teaching aerobics. But, I wore suits to work, and I think it was almost like I had 2 personas: the professional looking teacher and the slightly trashy looking gym instructor. Seriously, I was quite proud of my body, so I put it out there. I was only in my early to mid thirties, so it wasn't so inappropriate.