YA Books Like the Great Gatsby

My list of YA Books Like The Great Gatsby honors the 100th birthday of the original book. I have gender flipped YA Great Gatsby retellings, 1920s-set Great Gatsby books that feel like Gossip Girl, and a YA mystery that gave me all the Gatsby vibes!

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YA Books Like the Great Gatsby

Here are the qualities I’m looking for:

• a disillusioned or cynical narrator (or one who ends up that way)
• a rich friend and a bit of a power dynamic between the two
• over the top behavior
• a bit of a skewering of wealth and privilege
• bonus points for a 1920s setting

YA Books Like The Great Gatsby: Gender Swapped Great Gatsby Retellings

Self-Made Boys by Anne-Marie McLemore (2022)

Nicolás Caraveo is a teenaged transgender boy from the Midwest. He’s renting a modest house in West Egg from his cousin, Daisy Fabrega, who has erased her Latina heritage so she can pass as white.

Nick’s neighbor is a mysterious young man named Jay Gatsby, whose lavish mansion is the site of wild and extravagant parties. Jay has a secret: he is also transgender.

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Great by Sara Benincasa (2014)

Here’s my full review of Great

It takes moxie to tackle a retelling of a book that just about defines “Great American novel.” Great definitely has its strengths, like the clever gender-switching of many of The Great Gatsby‘s original characters, but in the end, teen angst in the Hamptons can never compete with the exquisitely-drawn blend of hope and despair that underlies the original story.

Nick Carraway has become … Naomi Rye? As in caraway seeds and rye bread? After that, I was expecting Jordan Bakery and Tom and Daisy Baguette to stroll onto the page. (No, that did not happen. Fortunately.) I also wasn’t crazy about the choice to turn war-weary Nick into a bland goth girl from the Midwest and Jay Gatsby into a quirky fashion blogger with a trust fund.

That said, there were definitely some things about Great that I really liked — namely, turning Daisy and Gatsby’s ill-fated love story into a fragile, furtive romantic relationship between two teenage girls. I thought that the relationship between Naomi and Delilah hit just the right note of doomed longing and, to me, felt true to the original story.

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YA Books Like The Great Gatsby The Gossip Girl Remixes

The Vixen series by Jillian Larkin (2010)

If you set Gossip Girl with the 1920s, you’d get Vixen. Gloria is engaged to Sebastian but she has a cousin with secrets and a resentful best friend.

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The Bright Young Things series by Anna Godberson (2010)

Letty and Cordelia are in New York City (and Long Island, of course) in 1929. Cordelia is our narrator figure, “searching for the father she’s never known, a man as infamous for his wild parties as he is for his shadowy schemes…” Well that sounds familiar!

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YA Historical Fiction Inspired by The Great Gatsby

A Sky Painted Gold by Laura Wood (2022)

Lou feels constrained in her quiet Cornish village and has big dreams of becoming a writer. The grand Cardew house near her home has stood empty for years, but when the owners arrive for the summer, Lou is amazed. Caitlin Cardew and her handsome, dashing brother Robert are sophisticated and dashing, sweeping Lou off her feet and into a world of late night cocktail parties and champagne.

But is there something darker lurking at the heart of the Cardew family? And as Lou gets drawn in by them, is she getting further away from all her goals and dreams?

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YA Fantasy Books with a Great Gatsby Vibe

The Diviners series by Libba Bray (2012)

Read my review of the audiobook of The Diviners

This book was 600 pages. The Great Gatsby was a slim 180 pages.

But if you want to understand the 1920s, this book will help you do that. To me, the most amazing part of The Diviners was the amount of historical detail included in the story.

This isn’t one of those books about the 1920s that just throws in a few flappers and a couple of Prohibition references and calls it a day. It’s clear that an enormous amount of research went into The Diviners, which not only features slang of the time but incorporates a lot of history — from the aftereffects of World War I to the Eugenics movement to1920s Harlem nightlife.

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The Curse Workers series by Holly Black (2010-2012)

Weird choice? I do think this amazing YA fantasy series has a few parallels to the Great Gatsby:

–Prohibition of illegal activity (alcohol/curseworking)
–Gatsby and Wolfsheim sell black market booze/Cassel is a grifter and con artist
–Cassel’s unrequited love for Lila/ Gatsby’s unrequited love for Daisy
–Strong sense of moral ambiguity (regular readers know how I love that!)

A YA Mystery With a Great Gatsby Feel

Liar’s Beach by Katie Contugo (2023)

You can read my Review of Liar’s Beach here!

This is technically a retelling of an Agatha Christie novel, but it did give me Gatsby vibes.

Our narrator is Michael Linden, a student-athlete who doesn’t belong at his preppy boarding school and certainly not in wealthy, storied Martha’s Vineyard. But when his roommate Jasper invites him to spend the end of summer at his massive beachfront home, August House, Linden tries his best to fit in.

When someone is found unconscious in Jasper’s pool, everyone has something to hide—Jasper, his beautiful sister Eliza, their older brother Wells, and their friends. The accident is written off as just that—an accident—but Linden begins to wonder…

This post by the NYPL has a list of Adult Books Like the Great Gatsby and Great Gatsby Retellings, so check it out!