Below is the complete list of Sara Shepard’s Penny Draws books in publication order. For this series, the chronological reading order is the same as the order of publication.
Penny Draws Books in Publication Order
- Penny Draws a Best Friend (2023)
- Penny Draws a School Play (2023)
About Penny Draws
Sara Shepard’s Penny Draws books show a very different side of her writing from the glossy suspense worlds that made her famous. Instead of secrets, lies, and high-stakes teen drama, this series turns inward and smaller in scale, focusing on everyday childhood worries with a warmth that feels unusually direct. The official series pages currently list six books, beginning with Penny Draws a Best Friend and continuing through Penny Draws a First Crush, and the through-line is clear from the start: Penny Lowry is a girl who doodles her way through fear, embarrassment, friendship trouble, and the constant overactivity of her own imagination.
That premise is simple, but it gives the books their real strength. Penny is not written as a larger-than-life comic heroine who bounces from mishap to mishap untouched. Her worries matter. The series is repeatedly described by the publisher as highly illustrated, humorous, and heartfelt, and that balance is exactly what makes it work. Penny’s doodling is not just a stylistic gimmick. It is part of how she processes anxiety and uncertainty, which gives the books emotional credibility underneath the jokes and visual playfulness. Sara Shepard is writing for younger readers here, but she does not flatten their feelings into something cute or disposable.
The first book, Penny Draws a Best Friend, establishes the series beautifully because it roots everything in ordinary school life. Strange smells, desk graffiti, social confusion, and family tension all feel enormous when you are a child, and the book understands that scale instinctively. Penny’s world is not dramatic in the thriller sense, but it is emotionally busy, which is exactly why the series feels lived-in. The worries may look small from the outside, but to Penny they are immediate and all-consuming, and Shepard takes that seriously without ever making the books heavy.
As the series continues through Penny Draws a School Play, Penny Draws a Secret Adventure, Penny Draws a Class Trip, Penny Draws a Team Sport, and Penny Draws a First Crush, the books widen naturally with Penny’s life. The subjects shift, but the emotional architecture stays steady. School performances, travel, sports, changing friendships, and first romantic feelings all create new forms of anxiety and excitement, and the series keeps returning to the same central truth: growing up often means learning that feelings can be ridiculous and real at the same time. That consistency is one of the line’s best qualities. Each book has its own hook, but the series never loses sight of who Penny is.
What makes Penny especially appealing as a lead is that she is not built around mastery. She is not there to dazzle the reader with confidence or to solve every emotional problem neatly by the final page. Her charm comes from how recognizably she spirals, imagines, overthinks, and keeps going anyway. The doodles help give that interior life shape. They let the books show how a child’s mind exaggerates danger, embarrassment, and possibility, which is why the illustration-heavy format feels so well matched to the character. These are books about feelings, but they are also about interpretation: how a worried kid sees the world, and how that vision can be funny, exhausting, and strangely creative all at once.
Within Sara Shepard’s bibliography, Penny Draws stands out as one of her gentlest and most accessible projects. It trades suspense for emotional immediacy and big reveals for small recognitions. That shift suits her well. The series has a softness that does not feel flimsy, because it is anchored in a believable child’s point of view. Read together, the Penny Draws books offer a warm, funny portrait of growing up anxious, imaginative, and hopeful, with each installment adding another small chapter to the larger work of figuring out who Penny is becoming.