Alright, here are the concepts I showed Chris.
http://i51.tinypic.com/d5wk6.jpg
Jack's got a gray hoodie, jeans, and brown boots. My idea was that as
he goes crazier throughout the game, his hair goes from an emover to a
complete train-wreck, and his hoodie gets covered with more and more
straps. Chris said that Jack will be getting more sane as the game
goes on, though, so the whole thing'll just go in reverse.
http://i56.tinypic.com/f4e5b7.jpg
For when Jack's sanity is totally gone (only during battle? I'm not
totally sure on how this will go down), his hood goes up everything
inside goes black, except for the two white eyes and solid white
smile. Sorta like a Cheshire Cat thing. At the bottom is an idea for
an attack, where Jack lifts up his hood and fires out his face like a
Bullet Bill.
As for how I'm going to draw this as a sprite, I'm still thinking
about it. Trying to pin down a style and all that. I'm making him
64x64 for the maps, so he'll be half the size the sprite in the game
is now. That should make him look a little better compared to the
trees.