These worked a little better, I had decided at this point that I would be designing the "Shoemaker's boy" character from The Tinderbox story. These characters look a little more child like than my others.
I quite liked the first paint over of this silhouette, though it really didn't fit with my time period, being the Persian empire. The rightmost design could work quite well however.
These designs all appear a little too mature looking to become a child character. That is, assuming the shoemakers boy is a child.

Having found the designs on the far left the most interesting, I decided to develop them and add more character in the form of clothing.