A successful real estate agent, Caroline is just 25, but she deliberately dresses as if she's 50. She is convinced her boxy, outdated skirt suits exude professionalism in the world of high-stakes New York City realty. Caroline thinks she only needs help with clothes to wear out with friends or on date, but Tim and Gretta are not convinced. They believe that Caroline's work clothes are limiting her ascent up the career ladder, however, Caroline's resistance to change may limit their ability to help. Fashion help from: hairstylist Orlando Pita and makeup artist Bobbi Brown.