"The Legend of Billie Jean" is the '80s-est '80s movie there is. It stars Helen Slater as Billie Jean, and she starts out with lovely long, blond hair. As seen above and below.
Look at that hair flow in the blowing wind as she rides with Corey Feldman on his super-cool scooter! (This scooter later causes trouble. In general, the plot of this movie is ridiculous and yet very empowering.)
So some things go down, and then Billie Jean is super mad, and she cuts off her hair and becomes an outlaw. That's right, an outlaw! And it's with that haircut that Billie Jean becomes a style icon.
She also rocks the one-earring look, which I am fascinated by. I could never wear only one earring as I would feel very lopsided, but I like how it looks on her in this context. (I also love it in this modern video by Matrimony.)
So, yes, Billie Jean. She ends up being a hero of sorts and looks good and tough and boyish doing it. Fair is FAIR! (That's their rallying cry. Fair enough.)