Maybe my version just lacks some files.
Take for example the scene where our girl enters the grocery for the first time.
I found the relevant files. On my disk I have:
View attachment 2550676
There is simply no picture with the girl in her blue sweater available.
And I just downloaded the game here and didn't delete anything.
groceryFirst2 is the picture with the "Default" outfit. In this case that'd be the sweater outfit. In an odd choice on my part I actually made the free dress Jill gives you if you go to the grocery store the default picture if it can't find your outfit for some reason so in this case the picture it is showing you is "groceryFirst2Free" when it should show you "groceryFirst2" which is the sweater outfit picture.
For future reference the naming scheme is:
<scene name + picture number> - default outfit. If it's before the makeover it's the sweater. If it's after it's the dress with the short jacket.
<scene name + picture number> + mesh - the outfit Jill gives you when you go on a date with her.
<scene name + picture number> + free - the outfit Jill gives you when you go to her store.
The reason you're getting the free dress instead of the sweater is because I accidentally set it to check for the makeup pictures and not the pre-makeover pictures. That's fixed now.
The other dress pictures are probably something similar. It'd be helpful if you tell me where in the game you're encountering it. There's enough content that finding them is a huge pain since the game is something like 150+ files now.