Matching the border was easy in illustrator. I scanned the title of a original book and found the font. I knew the art had to have some weird overlapping and perspective to it. The original cover artwork always had a painting/sketched feel to it. The back cover was B&W line art.
I really wanted the blue circles of the watch to the be the centerpiece...possibly a record. I did some initial layout sketches for cover art as well as some brainstorming for book titles and the back copy.