I called this “classic” to reflect its age, but honestly, it’s also Classic Rita in the emblematic sense. For me, her stuff almost exclusively seems to fall in one of two categories: inexplicable and strange, and stuff that’s a little eccentric but which she’s infusing with her cheeky brand of charm. This is squarely in the second camp. If she wore this today, we’d probably give her a hearty Well Played, and applaud her for showing up dressed as a person attending the funeral of a girl who tortured her in high school. She would slink in with a handkerchief, dabbing at her eyes, and then walk up and place her hand on the coffin. “Rest in peace, Tiffany,” she would say, grabbing a bottle of cold Diet Pepsi from her purse and then pouring it into the open casket, where she would then deposit her gum before sauntering out again.

[Photo: Getty]