The model for the Kit illustrations, Caitlin Waite (Imgur user cwaite13), recently posted behind-the-scenes photos online of her time modeling for the Kit illustrations. Here is the gallery:
Caitlin also shared about how she got the part online:
"Back in 1999, Pleasant Company had done some focus groups to determine the general look of the new Kit character, and landed on short blonde hair, blue eyes, and freckles. The artist that had been hired for the project was local to the Portland (OR) area, so they sent out a notice to the local modeling agencies. My headshot was submitted with the rest, and out of dozens of candidates they landed on me!
Every four months or so for the next two years I would get to take a week off of school to make each book (I was gone so much that one of my close friends actually pulled me aside one day to ask if I was sick and tell me that everyone was concerned for me, lol). They would send out a proof of the book with notes a couple weeks before the shoot to all of us modeling so we could get an idea for the context of each photo.
To create the final pictures, they would have us models act out the scene a few times (all posey-like) and the photographer would take a bunch of shots. Then the artist would take the photos and use them as the basis for an oil painting of the scene, picking out the best gestures or facial expressions or what have you from different photos. And then they would take photos (or scans?) of the oil paintings, scale them down, and that is what would end up in the book!"
Another fun fact Caitlin shared was that the pink cardigan outfit wasn't the original outfit they had in mind for Kit. "The original Meet Kit outfit [...] had a straw cap rather than the fabric beanie, and we shot the first book in its entirety with that outfit. Come to find out though, that when they started production on the doll version of the hat, the straw kept breaking on all of them. Cut to everyone scrambling, flying out to Pleasant Company office in Madison to reshoot everything with a new outfit and beanie, which is what you see in the book."
If you're reading this, Caitlin, thank you for this information! It is BEAUTIFUL.