In the season opener of "How Do I Look," Caleeta, a young aspiring makeup artist who despises her boyish figure has been layering on clothes and rocking a tutu to help give her curves. Her colorful, crazy and over-accessorized style is too much for her family--they even refuse to go out in public with her! Can Jeannie help this stick-thin gal create a voluptuous shape by wearing the right clothes? It's a fight to the end as Caleeta holds firm to her unique style--but will she have a change of heart?