Rihanna has a propensity for taking risks, whether they're personal, professional, or sartorial. The Barbadian singer will wear anything from ripped crop tops and trucker hats to floor-sweeping Dior couture, always accessorized with bold, ever-changing hairdos. She balances out her well-documented avoidance of pants with a taste for daring high fashion looks that even the most adventurous red-carpet-walker wouldn't touch, like Jean Paul Gaultier's wackier creations or a winged green bodysuit by Alexandre Vauthier. Even at her most casual, she always dresses fearlessly. Enjoy a look back at her fashion moments over the years.