Well, when my friends and roommates who like Guilty Gear and hoard pictures from it get up, I can ask about back view pictures of May. The shoes, I won't be much help on, though.
However, for the hat, try either supporting it with a thin craft foam or with an interfacing called Peltex, or something similar. Peltex is the almost card-board weight interfacing that people use to make handbags and fabric bowls.
I used it in a hat I made a couple years ago, and it helped immensely. It's going to cost quite a bit, though (where I am, non-fusible runs you $6 a yard, and it goes up $1 for each side you want fusible). You'd then just cover it in fabric. If it's not stiff enough when you're done, just spray on a spray-starch.