My teenage self loved Cluless. I was 15 when it came out and in the 10th grade so back then it was like the best thing since slice bread. I watched it once in my adult life and thought it was pretty dumb but I like the costume though I am not sure how many people would “get it”-it might more just look like you are wearing a cute outfit circa 1995.
I would totally ditch the dominatrix costume since you said it was a bugger to wear at home. I would go with Jane or Clueless. Maybe more clueless than Jane if you want to find someone to date.