Taylor Swift
Taylor Swift and her date did the bold thing of wearing exact matching outfits, but the baseball cap... That's not it. Either way, if the evening went well, hopefully, no song from the country-pop star came out of it.
Angelina Jolie
Jolie has never not been called the most beautiful woman in the world. Even from a young age, she was adorable. It doesn't matter if she went to prom with a date or not, she was definitely the best-dressed student there.