1990 Central High School, Philadelphia. Reader Kier writes “John Hughes would love this. Check the out the shoes. Very Ducky from Pretty in Pink.” Not gonna lie, when I looked at the preview for this picture there appeared to be a headless man in it. But no, it’s just couple who didn’t let a BIG difference in height get in the way of love. As my mom once said “They’re all the same height lying down.” Still cringing? You’re welcome.
The shoes are truly spectacular. His ensemble would only be improved if the tie I can’t see in this shot was a bolo tie. Rock this town inside out! Many girls would choose to wear a little shawl with a sleeveless dress just in case there was a chill in the evening air. But who needs a shawl when your gloves stop just shy of your armpits? Did they have the “little black dress approved” deodorant back in 1990? Because a white, chalky substance at the top of those suckers would be a damn crying shame.