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*Edit
Just wanted to add this wisdom from Pixar artist Jason Deamer, from his interview over at characterdesign.blogspot.com
"Once I've finished my research and I've got some interesting meat to sink my teeth into, I'll spend some time to think about the Who, What, When, Where, and the Why? This is a character in a story driven to act a certain way by the specifics of his or her circumstance. Who are they? When are they? What do they wear and how do they act? Does this person readjust their glasses every time they begin to talk. Is he/she a shy and timid sort of character? Maybe they hide behind long hair that covers their face? It's all of these character informed decisions that can really make a design speak to the viewer.
After finding some inspiration, I like to put all the research aside and try to capture a caricature through a kind of reverse osmosis from all the research I've done. I'll start doodling basic shapes, while always keeping the basic gesture of this character in mind. I'm looking for a simple form that captures the abstract feeling of the thing I'm trying to design.
When I find something that feels right I'll start to flesh that out into a silhouette of the character I'm after. At this point I'm focused not only on the pose but on the abstract relationships between the different basic shapes. How does the volume of the little leg feel relative to the mass of the torso? Is the head competing visually with the bag he's holding? Etc."
-Jason Deamer