If someone is grinning like a Cheshire cat, or is smiling like a Cheshire cat, they are smiling broadly, usually in a foolish way. Standing on the door step and grinning like a Cheshire Cat was Bertie Owen. He came indoors, smiling like a Cheshire cat, expecting to be congratulated. Note: You can also say that someone has a Cheshire cat grin or a Cheshire cat smile. I complained, but Jennifer stood there with her Cheshire cat grin. A beaming Steve stood in the background, nodding his head up and down and wearing a Cheshire Cat smile on his face. Note: The Cheshire cat is a character from `Alice in Wonderland' (1865) by the English writer Lewis Carroll. This cat gradually disappears until only its huge smile remains. The idea for the character may have come from Cheshire cheese, which was made in the shape of a smiling cat. Alternatively, it may have come from hotel signs in Cheshire, UK, many of which had a picture of a smiling lion on them.