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 :)
 
 
 
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