Personal stylist Rosie Pink moves to Chicago, where she starts her own business giving people fashion makeovers. She hires photographer Jaxon Brooks to take pictures of her and her clients, which helps promote the business. In return, she allows him to use the photos in his portfolio. Rosie and Jaxon get closer as they work together. Rosie's business takes off, and she helps her clients with their fashion and life choices. She also plays matchmaker with a few of her friends. However, when a new opportunity arrives in the form of a magazine stylist job, Rosie's schedule gets very crowded, and she has to decide what she really wants for herself.