The Boy in the Dress

Themes explored in this book: Identity, stereotypes, acceptance, friendship, family, kindness, empathy, loneliness.

Good morning! I decided to do some light reading this Saturday morning, and chose The Boy in the Dress by David Wailliams.

At first glance, The Boy in the Dress is a story about a boy and a bit of fabric. But David Walliams has tucked something much more meaningful between the pages—something that invites children (and adults) to look again at what makes us who we are.

Dennis is twelve years old. His best friend is a Sikh boy named Darvesh. He lives in a quiet house on an ordinary street and loves football passionately. But tucked alongside his love for the game is a fascination for fashion. When he finds himself wearing a dress for the first time—encouraged by the fabulously confident **Lisa—his world starts to shift. What follows isn’t just funny (although it’s properly funny in places); it is radical.

** "She was so gorgeous that probably even the hearts of squirrels missed a beat when she walked by." (p.110)

Walliams writes with a light touch, but there’s real heart beneath the humour. He doesn’t moralise, and yet he makes space for big questions: Why do clothes matter so much? Who decides what’s “normal”? And why are people so afraid of difference?

The emotional thread that stood out most to me was freedom. Not just the freedom to wear what you like, but the freedom to be truly seen. Dennis isn’t rebelling; he’s simply trying to express something real, something wordless, about himself. The dress becomes a doorway. And once he walks through it, he can’t unsee the world’s strange limits.

One moment stands out—when Dennis, disguised in a dress with makeup and high heels, is accepted without question by people who see only what he’s wearing. Dennis discovers dressing in a dress makes him feel good, not just different. It’s joyful but bittersweet. It reminded me how early children begin to hide parts of themselves to belong. And how much bravery it takes to stop hiding. Walliams captures this with ease and compassion.

Illustrations from Quentin Blake only add to the charm, making this a great pick for readers 8+, especially those beginning to question ideas about identity, creativity, or fitting in.

In the end, The Boy in the Dress offers something deceptively powerful: permission—permission to be playful, to be curious, and to be fully yourself—even when that self doesn’t fit the mould. I finished reading it in one sitting over a pot of hot coffee.

“I can be whoever I want to be! he thought.” (p.107)