The best books on tomboys by a historian of tomboys

Renée Sentilles Author Of American Tomboys, 1850-1915
By Renée Sentilles

Who am I?

As a young girl, I thought I was a tomboy—or I wanted to be one, because the image of a “normal” girl was far too pink and frothy and shallow for my tastes. For me, being a tomboy was less about being boy-like than being unable to claim the markers of femininity. As a historian of women and girls, I wondered how young women saw their futures in this modernizing America, with its True Women and New Women and the opening of advanced education. Did tomboys grow into the rebels who changed the world? Or, like the tomboys in so many fictional stories, did they renounce their assertive sense of self upon marriage and motherhood?

I wrote...

American Tomboys, 1850-1915

By Renée Sentilles,

Book cover of American Tomboys, 1850-1915

What is my book about?

American Tomboys is my answer to the question “when did it become a good thing for a girl to behave like a boy?”  Although “tomboy” had been around since the 1500s, it did not become a term for girls until the Civil War era, and then only in the United States. After reading over a hundred diaries and memoirs, as well as juvenile fiction, plays, songs, and newspaper features, I came to see that the tomboy who emerged in the mid-nineteenth century was both a transgressive and conservative figure, depending on the perspective of the reader. We know a tomboy when we see one, but at the same time her identity is ambiguous—and therein lies the power of the tomboy. 

The books I picked & why

Shepherd is readers supported. When you buy through links on our website, we may earn an affiliate commission. This is how we fund this project for readers and authors (learn more).

Little Women

By Louisa May Alcott,

Book cover of Little Women

Why this book?

This is the story of four sisters coming of age, but readers know that it’s really a book about Jo—the tomboy at its center. Jo March launched the tomboy as a quintessentially American girl icon, and Little Women launched the juvenile publishing market for girls. It remains one of the most beloved books in the world. I read it every year and always come away with something different.

Tomboy: A Graphic Memoir

By Liz Prince,

Book cover of Tomboy: A Graphic Memoir

Why this book?

I’ve assigned this graphic memoir to college students, given it to young nieces, and sent a copy to my mom. Prince tells the familiar story of being identified by others as a tomboy and struggling to understand what that means and whether or not she accepts the term. It’s funny, poignant, and smart.

You'll Grow Out of It

By Jessi Klein,

Book cover of You'll Grow Out of It

Why this book?

Comedian Jessi Klein explores the nexus of American femininity and female masculinity in this hilarious memoir. I particularly love her pithy statements on how commercial culture sells a somewhat toxic form of femininity that can make even the most female-identified person reconsider their gender. She cuts to the heart of the tensions of growing up in a culture that places gender on a spectrum but continues to market it as an extreme binary.

The Autobiography of a Tomboy

By Jeannette I. Gilder,

Book cover of The Autobiography of a Tomboy

Why this book?

Gilder’s memoir of growing up in the 1860s as a boyish girl will seem remarkably contemporary to those who equate nineteenth-century girls and women with corsets and overly important etiquette. Gilder writes about baseball, pranks, and various attempts to look like a boy, confirming an instinctual tomboy identity even at a time when females could not legally wear pants.

Tomboy: The Surprising History and Future of Girls Who Dare to Be Different

By Lisa Selin Davis,

Book cover of Tomboy: The Surprising History and Future of Girls Who Dare to Be Different

Why this book?

This one is for girls who want to know more about tomboys in the here and now. Davis essentially asks “how did we get to this time of transgender and nonbinary identity?” She interrogates the term “tomboy” as a way of understanding how our understanding of gender norms has changed and remained unchanged—at the same time.

5 book lists we think you will like!

Interested in tomboys, comics, and comedians?

5,309 authors have recommended their favorite books and what they love about them. Browse their picks for the best books about tomboys, comics, and comedians.

Tomboys Explore 12 books about tomboys
Comics Explore 118 books about comics
Comedians Explore 16 books about comedians

And, 3 books we think you will enjoy!

We think you will like The Billboard Bride, The Academy, and Louisa May Alcott: Little Women if you like this list.