Whitney Port Takes On New Job, New Guy, New Season Of 'The City'

Trailer for season two shows Whit working for Kelly Cutrone, Olivia working for Elle.

In the new season of "The City," set to return on September 29, Whitney Port faces a whole new set of challenges in the Big Apple. In the trailer for season two, we see that Port will have to learn to balance a new job, new co-workers and her old boss, while still pursuing her dream of being a fashion designer and maintaining a personal life.

Port has left the confines of Diane Von Furstenberg behind to work for Kelly Cutrone at PR house People's Revolution. Cutrone has offered her the job that would just take up "five, six hours a day" while she tries to get her fashion line off the ground. And in a gutsy move Whitney takes her designs to Cutrone to see if she has what it takes to be one of her clients too.

But all is not sunshine and roses for the ambitious designer and her boss. In the trailer some friction arises, as Port defends herself to Cutrone, and Cutrone is seen telling her, "I just hope that everything you do for all your friends — that they treat you as nice as you treat them."

Meanwhile, Port is also trying to move on from former flame Jay Lyon with a new guy named Freddy.

Whitney's former DVF arch nemesis Olivia Palermo also takes a new job at Elle magazine. But if fans know Olivia, they know that wherever she works, she's bound to butt heads. "I don't quit," she tells an Elle co-worker, and it sounds like a threat.

Watch the "The City" season premiere on Tuesday, September 29, at 10:30 p.m., right after the season premiere of "The Hills."