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So I have finally started designing my oval illustration for the book cover. Here I have presented a collection of screen-shots to show my progress on Rapunzel. 
The entire face was drawn free-hand in Photoshop using my graphics tablet. I then copied and pasted it into Illustrator, so that I could work around it to create the hair, which is all drawn using the pen tool and pencil tool. 
In order to make the plait of the hair into an even oval shape, I added a layer below the image and roughly sketched an outline to go by. For the end of the plait I wanted to do something more unique/unusual instead of just more hair, so I transformed the plait into petals...
I still have a lot more work to do this (e.g. finish off line work and add colour.)