Sean Penn has dated - and married - some of the most beautiful and iconic Hollywood stars of our time. You know you're doing something right in the dating world when you've dated Scarlett Johansson she doesn't even make it into your "Who Wore Him Better" feature because you've also dated Charlize Theron and Madonna.
Let's start with Madonna. These two were an iconic couple. They were together for 4 years, and their marriage was filled with passion and controversy - mostly due to Sean's temper. But even years after their split, Madonna called Sean the love of her life. On this particular day in the '80s, a much younger Madonna wore a much younger Sean Penn with a classic black and white ensemble, mysterious sunglasses, an edgy haircut and some very comfortable body language. Sean looks like your classic '80s bad boy in a leather jacket and awesome hair.
Skip ahead 25 years, and Sean is on the red carpet with Charlize Theron who absolutely slays in this yellow gown. Sean's looking a little shrimpy - but well-dressed - by her side in a all black look with an open collar.
It's hard for us to ever vote again Charlize on any matter since she is the queen of all things. But Madonna is Madonna. Madonna was the original here, and her comfortable loving body language with Sean, her iconic look, and the fact that we secretly want Sean and Madonna to reunite trumps all here. Madonna wins.