In the year after her mother Katherine ("Kat") Hudson's death, Charlie thought she had learned every secret her mother had. How could she have been so wrong? When Charlie discovers her mother's diary, it's as if Kat is right there, telling Charlie her story. Kat's story begins in 1965 when she's 19 years old―the beginning of the journey that teaches her that her life will only ever be as much as she is willing to settle for. She discovers that she is willing to settle for nothing less than her dream to become a fashion designer, regardless of the obstacles along the way.
Katherine Wilson Hudson is hell-bent on becoming a fashion designer. It's the mid-1960s, and everything about the decade smells of sex, drugs and rock and roll―but not in Kat's world. In her small-city life, her parents adamantly refuse to let her go to art school, instead insisting that she do what any proper '60's girls should do―become a teacher―and find a husband. Kat tries to be the "good girl" for two long years in university, but that doesn't sit well with her. When the opportunity for a scholarship presents itself, she ends up in New York City, a fashion design student at the prestigious Parsons School, the small-town girl trying to figure out where she really belongs.
Against the backdrop of the Vietnam War, race riots and the burgeoning women's movement, Kat must navigate the chasm between her seemingly superficial desire to be a part of the fashion world and the real-life choices that will ultimately define who she really is. When she finds herself at Woodstock, a weekend-hippie, she begins to realize that her grandmother was right when she told her that life would never be about finding herself. It would be about creating herself.
Determined to create the life she envisions, Kat faces one personal crisis after another before joining forces with an unlikely associate. And eventually figuring out who she is. "If you want to make god laugh," her grandmother, Fran, had told her, "tell her your plans."