If I Look This Good, Why Do I Feel Like Sh*t? takes us down the emotional super highway of Jessica, a half-Jew, half off-the-boat German who grew up in the South, went to college in New York City and briefly became a professional dancer that took her to Italy in a botched burlesque show. As she’s looking for the right outfit to wear to a pitch meeting and attempting to strike the right chord that dwells within the simple parameters of sexy, smart, and stylish, she lets us know that it’s not just the idea of a meeting in Hollywood – a place where women are forced into categories as tight as Scarlett O’Hara’s corset – her entire life has been defined by obsessing over what to wear and how to look. From her choices in men to her random career turns, she’s lived one long identity crisis. And in the re-living of it, Jessica explores what it takes for a woman to move past gender stereotypes, cultural ideals and personal roadblocks to ultimately find the holy grail of life: her voice.