Jessica Simpson spent some time with her mother Tina Simpson in New York City, New York on December 23, 2009. Jessica looked a little rumpled as she made her way out of her sister Ashlee Simpson-Wentz home with messy hair do and no make up as she headed to a midtown office building. When Jessica made her way out of the office building she let her hair down but still no make up as she made her way over to Ashlee’s Broadway show Chicago.