Ramona Quimby, Ramona the Pest
Beverly Cleary's 5-year-old heroine Ramona Quimby is better known as a trouble maker than as a style icon, but in the second book in the Ramona series she really comes out of her shell and shows us how trendy she can be.
First of all, Ramona was rocking a bob haircut before anyone in Hollywood got the 'do. In addition to having the hippest hairdo in kindergarten, the cover art of Ramona the Pest shows Ramona wearing her favorite shoes-- red rain boots. Let's remember that this book was written in 1968; years before Hunter rain boots appeared in America and made staying dry look good. Ramona clearly had some serious sartorial insight, even at age 5.
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