I photoshopped photos of them, merged the images together, and converted the file into Illustrator. The Silhouette Studio program will take .ai files, but not .jpgs. I traced the file and with some trial and error, made the portrait. I used some Amy Butler scrapbook paper for the background and created my own photo mat too.
I took this picture of Pearl on the same day. Yes, a gratuitous portrait of Pearl :)