Like most of us, celebrities make poor fashion choices from time to time. But unlike most of us, celebrities have deep enough pockets to not only purchase the best clothes, but pay stylists to tell them exactly what the best clothes are. So why is it that some stars make fashion mistakes over and over, year after year? We have no clue. But what we do know are fifteen examples of high-paid stars that have made a habit of making worst dressed lists, despite having the means not to.