Madonna at the 2013 Billboard Music Awards
Madonna has been rocking attention-grabbing outfits since before Lady Gaga was even born, and to this day she isn’t one to shy away from wearing something that would make your grandma avert her eyes. The look she wore to the 2013 Billboard Music Awards included platform heels, a faux fur jacket and a mesh skirt, proving that you don’t need pants to be a boss.