Questions re: Jill’s fashion choices:
1. Has she always dressed like this? If not, when did this weirdness begin?
2. If the white hats are, indeed, in charge, are they choosing her clothes for her, and if so, to what end? Is this some sort of messaging tool?
Removing tin foil hat now.....
I guess it's possible, but from observations, it looks like the only tool is Jill.
I think the weirdness began long, long ago, when she was photographed sitting quite cozily on Diaper Boy's knee. IIRC, he was married at the time. Not sure if she was still the batysitter at that time.