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One who is smiling smugly or mischievously. The term was popularized by the character in Lewis Carroll's Alice's Adventures in Wonderland. I knew he had a prank planned for April Fools' Day when he arrived at work grinning like a Cheshire cat.
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.
Having a perpetual, mischievous grin, one that is often indistinguishable from smugness. Although the Cheshire cat is best known as a character in Lewis Carroll's Alice's Adventures in Wonderland, it appeared much earlier in popular English culture, so the phrase may have originally referred to cheese made in the country of Cheshire and molded roughly to resemble a grinning cat. Lewis Carroll's feline had the ability to disappear until only its smile remained. The cheese variety would be sliced from hind end to front, which similarly gave the impression that its smile—if cheese showed emotion—would be the last to go.
Endangered Phrases by Steven D. Price Copyright © 2011 by Steven D. Price