What was she thinking!? A question that is asked repeatedly of female celebrities fashion choices following red carpet events. My study aims to look at the impact of this question and the gender issues behind it. Looking at best and worst dressed lists, I delve into the history and reasoning behind these degrading lists and think about whether there is a future for them. Using fashion theory, I consider why it is that people care about celebrity fashion, and why they are rated in these lists. I also cover the history of red carpet events and follow the evolution of tabloids and gossip magazines.