This is perhaps the most famous bob in the history of hairstyling. Anna Wintour has worn the cut for decades — from the age of 14, according to her Wikipedia page — and she doesn't show any signs of stopping. Here she is at the 2017 London Evening Standard Theatre Awards, sporting the iconic 'do along with a pair of shades, both of which are her signatures. In the YouTube video, Go Ask Anna, pop star Rihanna asked the fashion editor about her famous hairstyle and this is what she said: "The one time I tried to change it, it was a disaster. I had to wear a hat for several months. So I'm way too anxious and too lazy to try it again."