Mister Corporate Ladder!
These are some new sprites I made for the characters.
What I plan to do eventually is to have separate sprites for legs/pants, torsos and hair, and make the game dock them to the basic naked character sprite. Also the clothes/hair will be recolorable. Randomly generated NPCs will be given pairs of clothing/hair at random, but each piece of clothing/hair will probably have tags associated with it so the selection is more consistent with their personality. For example, emo characters will prefer dark clothing.
Of course this is all theoretical, and I may end up using a simpler system, although I hope I don't have to. This is too cool in my head!