Kitty Cheshire is a very mischievous girl who loves to cause trouble just like her mother, the Cheshire Cat. She is a Rebel because of unrevealed reasons.
As roommates, Wonderlandian friends and allies, Madeline and Kitty appear to be on good terms. Although Madeline befriends most of Kitty's enemies, the two are also friends with Lizzie, as the three share a close relationships as the future characters of Wonderland.
- “Hey Kitty. Can I ask you something? See, the narrators have been watching you and...”
- ―Maddie talks to Kitty.
Kitty and Cerise are seen as rivals. Like most of the students at Ever After High, they dislike her company, but she's a misunderstood Wonderlandian. Cerise initially was unaware of her secret being exposed in "The Cat Who Cried Wolf". However, in "Maddie's Hat-Tastic Party", Kitty somehow is unaware of her secret.
- “So, Cerise? Anything you would like to um, tell us?”
- ―Kitty confronting Cerise in front of everyone.
Duchess and Kitty appear to be acquaintances. The two are seen in the Castleteria and Madeline Hatter's Tea Shoppe in Kitty's Curious Tale. In Spring Unsprung, Kitty performed one of her pranks on Duchess, which surprised Duchess and she asked Kitty why she did it
- “Well there she is having tea with Duchess Swan, who is a Royal.”
- ―The Female Narrator observing Kitty and Duchess.
Lizzie and Kitty is known to be BFFAs, as they are seen as cameos throughout Ever After High and its background. And it was stated in Lizzie's diary that they have been friends since Nursery Rhyme. Though, in Kitty's diary, they had an argument then soon apologized to each other. The two seem to have an easygoing, communicative, and social friendship but in Lizzie Shuffles the Deck, Kitty is seen with the Rebels.
- “Crowns and Smiles under one tree.”
- ―Kitty in Lizzie's diary