In January 2009, it was announced that Hilary Duff would star in an indie feature, The Story of Bonnie and Clyde, an adaptation of Bonnie & Clyde. In April 2009, She began filming Provinces of Night, which is based on a book by the same name written by William Gay. She plays Raven Halfacre, the teenage daughter of a promiscuous, alcoholic mother. Hilary Duff has signed on for a 7-episode arc as Olivia Burke, a movie star who enrolls at NYU in search of a traditional college experience and ends up rooming with Vanessa (Jessica Szohr) in Gossip Girl.
In August 2009, it was announced that Hilary Duff 'll star in The Business of Falling in Love, a romantic comedy based on the book "Diary of a Working Girl," by Daniella Brodsky and directed by Gil Junger. The film is set to appear on the small screen for ABC Family. In the movie, Duff plays a fashion reporter who goes undercover in the business world hoping to find love while writing an article about dating men in suits. In September 2009, Duff released a second clothing line with DKNY Jeans as "Femme for DKNY." Hilary Duff decided to design a new clothing line for girls her age which had detachable scarves and adjustable belt loops.