While classically stylish, all-around good girls like Taylor Swift and Anna Sophia Robb tend to be touted in the press as parent-approved role models, it’s often the more rebellious stars that inspire trends in the fashionably-inclined. Take Miley Cyrus, for example—her twerking scandal of 2013 may have set her up as music’s requisite wild-child turned legal adult, but her platinum chop and brave styling of bralettes on the red carpet solidified her icon status (and inspired blonde bobs for several Lucky editors!).
The fashionably "bad" trend holds true for TV as well, as most of the small screen’s most stylish characters would have been undoubtedly dubbed terrible influences by our pearl-clutching mothers. In honor of My So-Called Life‘s 20-year anniverary today (all hail wild child Rayanne Graff!), we put together a list of our five favorite TV frenemis. Click through the slideshow above to see who made the cut—and how to cop their style.