Cheshire Cat Smile – An Innocent Grin or a Smug?

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Alison Page

Alison has worked full-time in the writing industry for over ten years, using her knowledge and life experience to create online content, fiction and non-fiction. Alison has published two novels and has ghost-written several non-fiction equestrian books for a client. Alison has been a full-time professional content writer for almost ten years and loves her work as a wordsmith.

Cheshire cat smile or grin like a Cheshire cat is an idiom that means to smile very broadly at someone or something, typically in a smug or secretive way.

Idioms, such as Cheshire cat smile or grin like a Cheshire cat, involve figurative language, where words take on meanings distinct from their literal interpretations. We use them in everyday informal speech to create analogies, and learning them helps us to master the English language’s many nuances.

This article explores the idiom’s meaning, variations, origin, synonyms, antonyms, and different contexts for its usage. We’ve also included a fun quiz to test your knowledge. 

Continue reading to discover how to incorporate the idiom Cheshire cat smile into your everyday speech and writing.

Cheshire Cat Smile – An Innocent Grin or a Smug

What Does the Idiom Cheshire Cat Smile Mean?

The idiom Cheshire cat smile refers to a broad and often mischievous or enigmatic smile. In some definitions, it’s stipulated that the smile should be broad enough to expose the gums.

When someone grins like a Cheshire cat, it often suggests smugness or self-satisfaction, as the grinner is privy to information unknown to the onlooker. Another connotation of the idiom is that the smile might have slight malevolence.

According to the Collins Dictionary, grin like a Cheshire cat means “to do a big smile, often because you are pleased with yourself.” defines the idiom as “to smile broadly, especially in a self-satisfied way.”

Note that the word Cheshire is capitalized since it’s a proper noun.

Variations of the Idiom

There are a few variations of the idiom grin like a Cheshire cat or Cheshire cat smile, including the following:

  • Grins like a Cheshire cat
  • Smile like a Cheshire cat
  • Grinning like a Cheshire cat
  • Smiling like a Cheshire cat

How Is Cheshire Cat Smile Commonly Used in Context?

Cheshire cat smile or grin like a Cheshire cat is an informal expression typically used in everyday conversation or informal writing. You can use the idiom casually in conversation for the most impact. Remember that context might be necessary for non-English speakers to understand exactly what you mean in writing and speech.

What Are the Different Ways to Use Cheshire Cat Smile?

  • Literal description: “Emori greeted me with a Cheshire cat smile, leaving me curious about her thoughts.”
  • Mischievous expression: “As Lexa shared the news, a Cheshire cat smile revealed her mischievous delight in the surprise.”
  • Mysterious grin: “That’s a Cheshire cat grin. What are you hiding?”
  • Sly or smug grin: Abby offered him an enigmatic, Cheshire cat smile, leaving Monty wondering what or how much she knew about his criminal activities.

Where Can You Find Examples Of Cheshire Cat Smile?

Although informal and casual, Cheshire cat smile or grin like a Cheshire cat is a popular idiom. You’ll find them used in everyday conversation, as well as many of the following media:

  • Literature
  • Movies and TV shows
  • Songs
  • Conversations and personal anecdotes
  • Online resources

Here are some examples of the idiom’s use:

Leigh Griffiths admits he is purring at the prospect of being back among the cream of Europe – and it’s no wonder Peter Lawwell is still grinning like a Cheshire cat. (The Scottish Daily Record)

He smiled like a Cheshire cat and said, ‘It’s been 20 years. They haven’t caught me yet’; she said of a conversation she had with her father when he was in jail in New York in December 2012, awaiting trial for the murder of his son, Levi Karlsen. (The Calaveras Enterprise)

What Are Some Tips for Using Cheshire Cat Smile Effectively?

The idiom Cheshire cat smile is generally used metaphorically to convey a sense of playfulness, mystery, or inscrutability. 

Here are some tips for effectively using the idiom in your conversation and writing:

  • Use appropriate context: The idiom can be used when someone is grinning broadly and knowingly.
  • Send a clear message: Clearly stress the fact that the smile is enigmatic or mysterious when you say someone has a Cheshire cat smile.
  • Avoid overusing the idiom: Overusing the idiom can dilute its impact, so reserve it for occasions when the person’s character might mean they have a Cheshire cat smile.
  • Know your audience: Be sure your audience understands the idiom or explain the context to them.
  • Use it in conversational phrases: When using this idiom in a piece of writing, be sure it fits the tone and style of the article or blog post.
  • Understand the idiom’s meaning: Understand that the idiom could be construed as mildly offensive if you use it to mean that someone is smiling smugly or could be hiding something from others. So, know your audience before using it to describe someone.

What Is the Origin of the Idiom Cheshire Cat Smile?

Cheshire Cat Smile Ngram
Cheshire cat smile usage trend.

The idiom Cheshire cat smile is commonly associated with Lewis Carroll’s 1865 children’s book Alice’s Adventures in Wonderland. The Cheshire cat is portrayed as inscrutable in the story and disappears, leaving only its creepy smile behind. For that reason, the expression grinning like a Cheshire cat can have slightly sinister undertones.

The term grin like a Cheshire cat predates the publication of Alice’s Adventures in Wonderland by at least 75 years, if not longer. Cheshire is a county in England known for its milk and cheese products, which is surely a reason for Cheshire cats to smile. There are various stories about painted signs depicting poorly drawn lions in Cheshire County in the early 1800s.

The most intriguing story may be that at one time, a cheese shaped like a cat was manufactured in Cheshire County. The cheese was eaten from tail to head, leaving the cat’s smile as the last part of the cheese to be consumed. How cheese sellers induced their customers to cooperate in their method of cheese-eating is unrecorded.

How Did the Idiom Evolve Over Time?

The idiom Cheshire cat smile evolved over time as Lewis Carroll’s Alice’s Adventures in Wonderland gained popularity. The Cheshire cat’s distinctive grin, persisting in the absence of its body, became a symbol of mysterious and lingering smiles.

Over the years, the expression entered common usage to describe a smile that remains after someone has departed, suggesting an enigmatic or elusive quality. The idiom has since maintained its association with a smile that lingers or appears detached from its context.

What Are Some Related Terms to Cheshire Cat Smile?

To fully understand its idiomatic use, you should pay close attention to context and fully understand the meaning of the expression. Knowing the related terms can help you better know how to define the idiom properly.

Cheshire Cat Smile – An Innocent Grin or a Smug 1


  • Smug grin
  • Cunning smile
  • Mischievous grin
  • Wry smile


  • Frown
  • Scowl
  • Serious expression
  • Stony-faced
  • Pout

Cheshire Cat Smile: Test Your Knowledge!

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Let’s Review

Cheshire cat smile is a well-known idiom in English. Idioms are words or phrases that are illogical outside of their regional or cultural context.

In the case of this idiom, when you say someone has a Cheshire cat smile or is grinning like a Cheshire cat, you mean they are smiling or grinning broadly, possibly in a smug or self-satisfied way, as though they are keeping a secret.