The best romance books featuring tomboys

Why am I passionate about this?

Having climbed many a tree with the boys as a kid, I cannot stay away from a good gender-bender romance. The suspense, the humour of it, and the inevitable conclusion that not your appearance but your choices define who you are – a perfect combination in my opinion. Mix in a male counterpart who is supportive and understanding and I am hooked! So much so, that I have written a book about a girl who dressed up as a boy.


I wrote...

The Girl Who Was a Gentleman

By Anna Jane Greenville,

Book cover of The Girl Who Was a Gentleman

What is my book about?

London, 1872. In Victorian England, a woman’s only hope is to marry well, but who would want a penniless wife? Joanna doesn’t believe in fairy tales, and chooses to be her own prince. She decides to pursue a career of her own by attending the prestigious Oliver Kenwood Boarding School – disguised as a boy. 

If only it weren’t for her cunning yet fascinating teacher Charles Hanson who seems to dislike her quite passionately. With him watching her every step, she finds it increasingly difficult to hold up her disguise, particularly when rich and confident Abigail sets her eyes on Hanson – why does it bother Joanna quite so much? And is her secret really as safe as she hopes?

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The books I picked & why

Book cover of The Corinthian

Anna Jane Greenville Why did I love this book?

Love is not the only thing that is in the air in this one. Penelope happens to dangle off a window in boy clothes just when Mr. Right comes passing by.

If Heyer's romance books were a food, they would be red velvet cupcakes – sweet and elegant. I have yet to read one of hers that is not amazing.

By Georgette Heyer,

Why should I read it?

1 author picked The Corinthian as one of their favorite books, and they share why you should read it.

What is this book about?

The only question which hangs over the life of Sir Richard Wyndham, notable whip, dandy and Corinthian, is one of marriage. On the eve of making the most momentous decision of his life, he is on his way home, a little worse for drink, when he chances upon a beautiful young fugitive climbing out of a window by means of knotted sheets - and so finds a perfect opportunity for his own escape.


Book cover of Bloody Jack

Anna Jane Greenville Why did I love this book?

Mary "Jacky" Faber, an orphaned street kid in early 19th century London, begins her adventures across the seven seas by dressing up as a ship's boy. Throughout the series she builds up quite the amazing resume that would put a Navy Seal to shame. And of course, there is a bit of romance here and there but the focus lies on Jacky sailing the world and kicking butt!

By L. A. Meyer,

Why should I read it?

2 authors picked Bloody Jack as one of their favorite books, and they share why you should read it. This book is for kids age 13, 14, 15, and 16.

What is this book about?

Life as a ship's boy aboard HMS Dolphin is a dream come true for Jacky Faber. Gone are the days of scavenging for food and fighting for survival on the streets of eighteenth-century London. Instead, Jacky is becoming a skilled and respected sailor as the crew pursues pirates on the high seas.
There's only one problem: Jacky is a girl. And she will have to use every bit of her spirit, wit, and courage to keep the crew from discovering her secret. This could be the adventure of her life--if only she doesn't get caught. . . .


Book cover of The Academy

Anna Jane Greenville Why did I love this book?

A somewhat different kind of setting awaits readers in The Academy. It depicts a dystopia in space that resembles Victorian times quite strikingly. Pretty awesome combination, huh? The heroine infiltrates an all-boys school to become a spaceship pilot and navigate the stars. Only to discover even the galaxy is not big enough to run from love.

By Emmaline Andrews, Reese Dante (illustrator),

Why should I read it?

1 author picked The Academy as one of their favorite books, and they share why you should read it.

What is this book about?

The Academy
Where things are not always as they seem…

My name is Kris Jameson and I’m a student at the Royal Academy. I’m at the top of all my classes, what they call a “model student.” There’s only one problem—the Academy is an all boys school and I’m a girl.

It started as a prank when I took my brother’s place. But things got complicated when I caught Broward, the school bully, in a compromising position. They got even worse when I was assigned my roommate—the handsome but enigmatic North who saved me several times from the bully’s attacks.…


Book cover of Louisa May Alcott: Little Women

Anna Jane Greenville Why did I love this book?

Why I recommend this book that every romance-head can recite cover to cover? Because I could not possibly take myself seriously as an author if I didn't. Seriously, Jo is a tomboy legend. She does not even need to get dressed up as a boy to show us who’s boss.

By Louisa May Alcott, Roberta Bordone (illustrator),

Why should I read it?

1 author picked Louisa May Alcott as one of their favorite books, and they share why you should read it. This book is for kids age 7, 8, 9, and 10.

What is this book about?

An adapted and illustrated edition of Louisa May Alcott's Little Women, at an easy-to-read level for all ages!

‘Happiness doesn’t come from money,’ said Mrs March. ‘I’d rather see my girls happy and married to poor men, than unhappy and married to rich men.’

The March sisters are living through tough times. Their father is off at war, money is scarce and the eldest sisters must work to support their mother. Their poverty creates hardship to be overcome. But will the girls grow to find richness of spirit as well as material wealth?

About the Sweet Cherry Easy Classics series:…


Book cover of The Twelfth Night; Or, What You Will

Anna Jane Greenville Why did I love this book?

Twelth Night or, What You Will just has to be on here, being the mother of all boys-clothes-wearing heroines. The plot has been adapted in so many books and films that it is definitely worth it to read the original (or better yet: watch the play) to see where the brilliancy stems from.

By William Shakespeare, William J. Rolfe,

Why should I read it?

1 author picked The Twelfth Night; Or, What You Will as one of their favorite books, and they share why you should read it. This book is for kids age 10, 11, 12, and 13.

What is this book about?

Part of the "Everyman" series which has been re-set with wide margins and easy-to-read type, this book includes an introduction and comprehensive notes. This is Shakespeare's "Twelfth Night".


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Split Decision

By David Perlmutter,

Book cover of Split Decision

David Perlmutter Author Of The Encyclopedia of American Animated Television Shows

New book alert!

Why am I passionate about this?

I am a freelance writer from Winnipeg, Manitoba, Canada, specializing in media history and speculative fiction. I have been enchanted by animation since childhood and followed many series avidly through adulthood. My viewing inspired my MA thesis on the history of animation, out of which grew two books on the history and theory of animation on television, America 'Toons In: A History of Television Animation (available from McFarland and Co.) and The Encyclopedia of American Animated Television Shows (available from Rowman and Littlefield). Hopefully, others will follow.

David's book list on understanding the history of animation

What is my book about?

Jefferson Ball, the mightiest female dog in a universe of the same, is, despite her anti-heroic behavior, intent on keeping her legacy as an athlete and adventurer intact. So, when female teenage robot Jody Ryder inadvertently angers her by smashing her high school records, Jefferson is intent on proving her superiority by outmuscling the robot in a not-so-fair fight. Not wanting to seem like a coward, and eager to end her enemy's trash talking, Jody agrees.

However, they have been lured to fight each other by circumstances beyond their control. Which are intent on destroying them if they don't destroy each other in combat first...

5 book lists we think you will like!

Interested in tomboys, Pirates, and William Shakespeare?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about tomboys, Pirates, and William Shakespeare.

Tomboys Explore 19 books about tomboys
Pirates Explore 85 books about Pirates
William Shakespeare Explore 178 books about William Shakespeare