Yeah, in high school I would have been voted least likely to go preppy. But then I had no style whatsoever. Sure I wore some 80's weird stuff and had a spiral perm with moused poufy bangs. But basically I dressed pretty blah and nondescript. My parents didn't emphasize appearance and I didn't feel I could measure up to the pretty girls. So I mostly dressed ultra casual and concentrated on deeper things . . . like boys. Fast-forward 25 years or so and here I am playing prep for the day.
For some reason this vest cried out to me one day as I was browsing a thrift store. It was so tiny that I thought it must be mis-sized . . . but then my newly fashion-oriented brain thought "hey, waist definition!" I did have to tug it back down to waist level a few times and took to calling it "the world's smallest vest" by afternoon. Still, it was basically comfortable and fun to wear. Another funny thing--it had a tiny Tommy Hilfiger emblem at the waist and I kept picking at it thinking there was a little speck on my sweater.