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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I Meant to Tell You

By Fran Hawthorne,

Book cover of I Meant to Tell You

Fran Hawthorne Author Of I Meant to Tell You

New book alert!

Why am I passionate about this?

Author Museum guide Foreign language student Runner Community activist Former health-care journalist

Fran's 3 favorite reads in 2023

What is my book about?

When Miranda’s fiancé, Russ, is being vetted for his dream job in the U.S. attorney’s office, the couple joke that Miranda’s parents’ history as antiwar activists in the Sixties might jeopardize Russ’s security clearance. In fact, the real threat emerges when Russ’s future employer discovers that Miranda was arrested for felony kidnapping seven years earlier—an arrest she’d never bothered to tell Russ about.

Miranda tries to explain that she was only helping her best friend, in the midst of a nasty custody battle, take her daughter to visit her parents in Israel. As Miranda struggles to prove that she’s not a criminal, she stumbles into other secrets that will challenge what she thought she knew about her own family, her friend, Russ—and herself.

I Meant to Tell You

By Fran Hawthorne,

What is this book about?

When Miranda’s fiancé, Russ, is being vetted for his dream job in the U.S. attorney’s office, the couple joke that Miranda’s parents’ history as antiwar activists in the Sixties might jeopardize Russ’s security clearance. In fact, the real threat emerges when Russ’s future employer discovers that Miranda was arrested for felony kidnapping seven years earlier—an arrest she’d never bothered to tell Russ about.

Miranda tries to explain that she was only helping her best friend, in the midst of a nasty custody battle, take her daughter to visit her parents in Israel. As Miranda struggles to prove that she’s not…


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 179 books about William Shakespeare