Shortly after, the began working for Kelly Cutrone's People's Revolution, a PR firm heavily involved in the fashion industry.
She had also modeled Hilary Swank's dress from the 2005 Academy Awards on a live Good Morning America segment with André Leon Talley, the editor-at-large of Vogue magazine.Port's Teen Vogue supervisor and editor Lisa Love praised her for handling the incident with class and grace. She has also been featured on the covers of Cosmopolitan, Teen Vogue, Seventeen, and Rolling Stone (with fellow castmates Lauren Conrad, Heidi Montag, and Audrina Patridge,) among others.Prior to working at Teen Vogue, Port was an intern for the Women's Wear Daily magazine for two summers. In 2006, Port was cast as one of four main cast members in the MTV reality series, The Hills, which saw her interning for Teen Vogue for the first three seasons.The first season saw her primarily at the workplace, with the season concluding as Port accepts a summer internship in Paris that had been declined by fellow intern and castmate Lauren Conrad.However, the series was renewed for ten additional episodes, which saw the addition of several new cast members, including Port's friend Roxy Olin, as well as her return to People's Revolution.
featured Later, MTV renewed The City for 10 more episodes to season one, which premiered September 29, 2009.
She was offered, and accepted, a position at People's Revolution, becoming co-workers with Port once again.
In the fourth season of The Hills, Port began dating Jay Lyon, and was offered the opportunity to move to New York to pursue a career in high fashion at Diane von Fürstenberg.
In March 2008, Port debuted her clothing line of cocktail and partywear called Whitney Eve.
The clothing line was in the New York Fashion Week in September 2009, in the Spring/Summer 2010 season.
In 2008, she received her own spin-off series, The City.