As high school graduation nears, Wren Gray is surprised to connect with gentle Charlie Parker, a boy with a troubled past who has loved her for years, while she considers displeasing her parents for the first time and changing the plans for her future.

Winnie's celebrates her unique style through her first year with a double-digit age as she has many new experiences, from the high of spending time in New York City with her aunt and big sister, to the low of her two best friends suddenly becoming interested in boys.