Chanel's pistol heels have made their way onto the feet of a few bold celebrities. The queen of experimentation, Madonna, wore hers back in October with a black Dolce & Gabbana dress. The chiffon fabric of her frock helped downplay the roughness of the heels. Ashlee Simpson also rocked Chanel's pistol heels during a night out in LA. She opted for a more casual approach by wearing a striped tee and black flowy skirt. Both ladies clearly love funky footwear, but who pulled this one off more naturally?