I'd say for Loretta and Stella's portraits in-game wise that you posted Johann, move their heads down a bit. Right now you're seeing more of their neck and outfit than their actual face. Especially Stella, that neck is taking up most of the portrait.
Otherwise I think with some tweaking here and there in their in-game portrait form, these could work incredibly well!
Keeping it like that for Loretta means the awkward perspective of the bonnet is avoided.
I'll try to move Stella down a bit. I hope I can remember by what percentage I scaled down so I only have to retouch the top part and can salvage the rest.
new v old
Like both Charlotte and Morris' current images don't have some sort of side view, like the rest of the portraits, so they look a bit off.
Jonathan is somewhat sideways. It's mostly Charlotte, Vincent and Brauner who are front-facing.
The original portraits were rather inconsistent about this as well. Both Brauner and Dracula were depicted front-view.
Only one I might further modify is Death.
For some reason, the skinny skull doesn't fit well for me, I:ll try to see if I can find a more prominent/rectangular shaped skull for Death to go along his portrait.
It's the only suitable skull I remember finding among Kojima's art, but I suppose any realistically illustrated skull would do.
Edit: A first rough version of the ending portraits. I assumed they shared a palette.
I went with a gold leaf background for the good ending Vincent portrait. I feel like that translated well.
The black Kojima gouache background isn't very recognizable on the other portraits, unfortunately.
Here's an alternate portrait for Charlotte from grimoire of souls
Oh, I totally forgot about Grimoire of Souls since it still hasn't been released. I'll see if I can cobble together a new Charlotte based on that (the arm is positioned a little unfortunately, but that's probably an easy fix)