Jen teaching, pajamas outfits
At a minimum, the plot of Leona Wish is going to call for two additional outfits: a teaching outfit and a pajamas outfit.
We currently only have Jen's casual outfit integrated into the game. Her source game still has a teaching outfit we can repurpose, though due to all the modifications we made it might not be completely trivial.
The other outfit is essentially from scratch. We need some kind of sleepwear outfit. Jen does not have a nude sprite so this will take a decent amount of work. If we want more flexibility, we could potentially start with a nude sprite, then move on to an underwear or sleepwear sprite.
Existing teaching outfit:
For the sleepwear outfit, I'm have a "camisole and shorts" sort of thing in mind. It should definitely look more on the "comfortable" side than the "sexy" side. Something along these lines: