Books about Underwear
There are some topics that kids never seem to outgrow, and books about underwear is definitely one of them! I can’t tell you how many times I pulled out one of these books during read-aloud and watched even my most reluctant listeners scoot a little closer to hear what would happen next. If you’re looking for books that make kids laugh while encouraging discussion and a love of reading, these are some of my favorites.
Why Underwear Books Are a Classroom Favorite
Kids love books about underwear because they are unexpected, silly, and just a little bit mischievous. These stories grab attention, encourage reluctant readers, and often lead to great conversations, laughter, and imaginative play.
Teachers love these books for many of the same reasons students do, but they are also wonderful for sparking discussion, inspiring silly writing projects, and encouraging creativity..
Underwear books are guaranteed to get kids giggling, but they’re also surprisingly versatile! They’re especially fun at the beginning or end of the school year, right before school breaks, during indoor recess, or when you need an engaging read-aloud for a substitute teacher. They also make great conversation starters for social-emotional learning (SEL) discussions and are a wonderful way to capture the attention of reluctant readers.
Which Books about Underwear Should We Read?
Whether you’re looking for a laugh-out-loud read-aloud, a fun writing prompt, or a book to brighten a rainy day, these underwear-themed books are sure to be a hit.
Silly Books about Underwear







Santa’s Underwear by Marty Rhodes Figley
It’s Christmas Eve, and Santa can’t find his favorite Christmas underwear! He tries on every other pair he owns, but nothing feels right. Just when he’s about to give up, his reindeer surprise him with something special. Ho ho ho!
Underwear! By Jennifer Harney
A tired bear dad tries to get his rambunctious cub to bed — but the cub would rather play with his underwear! Underwear makes great hair, a superhero cape, and even swimming goggles. A fun rhyming bedtime story full of wordplay!
The Underpants Books by Claire Freedman
This hilarious series has everyone loving underpants! Dragons knick-knack their way through the Kingdom of Pantasia, dinosaurs go extinct in an Underpants War, aliens visit Earth just to steal your underwear, pirates set sail for underpants treasure, and monsters show off their best pairs at a secret Saturday night dance.
💚Grab the extension idea for Aliens Love Underpants on TPT.
Underwear Books With Heart




Hedgehogs (Don’t) Wear Underwear by Marissa Valdez
Jacques is a little French hedgehog with a big secret — he loves wearing underwear! But hedgehogs have rules, and underwear is definitely not on the list. Will Jacques find the courage to embrace his love of underpants?
Those are Not My Underpants! by Melissa Martin
Bear Cub finds a pair of underwear hanging in a tree and sets off through the forest to find the rightful owner. Could they belong to Squirrel? Moose? Snake? Salmon?! Readers will be giggling the whole way — especially when they find out who they actually belong to!
Something’s Wrong!: A Bear, A Hare, and Some Underwear by Jory John
Jeff the bear has definitely forgotten something. He ate breakfast, watered his plant, combed his fur — but something still feels off. Could it possibly have anything to do with the fact that he’s wearing his underwear over his fur?!
Underwear! by Marie Elis Monsell
Zachary Zebra and Orfo Orangutan love the World’s Greatest Grassland Underwear Fair — but Bismark Buffalo is always sad and grumpy. Until the other animals hatch a plan involving underwear that just might change everything!
Brave and Slightly Scary Underwear Books



Attack of the Underwear Dragon by Scott Rothman
Sir Percival is a great knight — except for one small fear: the Underwear Dragon! When the unthinkable happens, Cole, the assistant knight, is the only one left to save the kingdom. Luckily, an unfortunate underwear mishap saves the day!
The Underwearwolf by Gideon Sterer
Whatever you do — do NOT wear this underwear under a full moon! One rule-breaking kid ignores the warning and transforms into an Underwearwolf! What follows is an unforgettable nighttime adventure full of furry paws, sharp claws, and very uncomfortable wedgies
Creepy Pair of Underwear! by Aaron Reynold
Jasper Rabbit is NOT scared of anything — especially not underwear. But when his new undies glow a ghoulish green in the dark, suddenly he’s not so sure. No matter how hard he tries to get rid of them, they just keep coming back!
💚Grab the extension idea for Creepy Pair of Underwear.
Underwear Books for Problem Solvers


Return of the Underwear Dragon by Scott Rothman
After saving the kingdom, Sir Cole realizes the Underwear Dragon simply cannot read. Together, they take on a new challenge in this funny story about learning and perseverance.
Stone Underpants by Rebecca Lisle
Pod’s bottom is bare and there’s a cold wind blowing! He tries making underpants out of different materials — starting with stone — but each one has its own hilarious drawbacks. Will he ever find the perfect pair?
Vote for Your Favorite Underwear Book
After reading a few of your favorite underwear books, let students vote to decide which stories deserve a special award! Encourage them to defend their choices by explaining why a particular book was the funniest, silliest, scariest, strangest, cutest, or simply their overall favorite. It’s a fun way to build speaking and listening skills while giving every student a chance to share their opinion. To make it even easier, I’ve included FREE printable book award certificates for your class to use.
💚 Grab your FREE Underwear Awards here!


Some books make kids laugh instantly — underwear books always seem to do the trick. Whether you read one or make your way through the entire list, I hope you find a few favorites to enjoy with your students or family.
Which underwear book would win in your classroom? Let me know in the comments below!
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