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About the hair, I want this character to be kind of androgynous so that regardless of who's playing, they can see themselves as this character. She is canonically a girl, but I don't want to make her any more feminine than she already is. Plus it has some lore relevence, but that's something of a spoiler.
But the crotch split is something I'll have to look into. I believe the way I designed it has something to do with the references I was using, which had a different colored middle secton on the dress for many of them. It does read kind of awkwardly, so I'll see if a slight redesign could help.
The tiara is good but I can't quite make out the face. The hair might as well be a man's hair. She has shoulderpads and what looks like a coat. I don't quite understand the thick vertical line in the crotch. Without a footnote that says "princess", I'm not seeing anything to indicate that she's feminine. Of course, I understand that femininity is not easy to communicate with 30 black and white pixels without giving her balloon breasts. Depends what kind of style you're going for. 
Edit: I realize you want them to work on either black or white background, I just wanted to get the point across.
What about the princess has poor readability?
And thanks! I went on a design spree a good while ago and I really fell in love with designing sets for this project. I'm hoping to do more, even if they don't end up in the final game.
Nice! Other than the princess, I think they all have good readability and/or shapes that leave a lot of room for the imagination. 
Alrighty.