#8: Diana Spencer Wearing Her Revenge Dress, 1994
Not all little black dresses are created equal. Princess Diana might have had the best little black dress moment ever when she stepped out in her famous (or infamous) “Revenge Dress.” Lady Di wore this iconic dress to the Vanity Fair party on June 29, 1994, and she wore it with good reason.
As Diana was stunning everyone in this dress, her then-husband was admitting to cheating on her on international television. It’s no coincidence that she decided to turn heads and drop jaws in this Christina Stambolian number. This piece of fashion history is so famous that it even has its own Wikipedia page. No, we’re not kidding.