I'm so old, when I was in HS, we were just about transitioning from little Villager dresses and Nantucket basket purses to Landlubber bellbottoms with midriff tops and leather sandals .
I bought a pair of those red PF Flyers high tops when I was in my early thirties and in my "aerobics instructor" phase. I wore them one day with a turquoise sundress with a red sleeveless t shirt under and my DH told me I had gone "a little too far" for a mother of 2 young kids. Seriously, I did look a little weird. I traded in the high tops for a pair of funky red canvas flats that I wore until they fell apart.