Villains Join The Princesses School

The premise does the work here. Put a villain in a princess school and the whole question becomes how much she is willing to blend in.

That gives every outfit a point of view. Full uniform and she has surrendered. Full villain and she is not really attending. The interesting looks are in between, where a school silhouette carries villain colours, or a perfectly correct uniform is undone by one accessory that should not be there.

It is a better dress up game than the title suggests, because you are answering a question rather than filling a mannequin. Try building the same character twice, once trying to pass and once refusing to, and see which one you keep.