Starting with her birthday in March, every chapter brings a new month and a new event in Winnie's life. From surviving her teenage sister's grumpy mood swings in April to dealing with prissy new rival Gail Grayson in September, there's a calendar full of the ups and downs of being eleven years old. Especially hard for Winnie is the growing distance between herself and her best friend, Amanda, as both girls grow into different social circles. The big...

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.