Outfits Not Updating

I'm having an issue with a Sim on my new Lovestruck play through save file. My original Sim met a gallery Sim on Cupid's Corner who has since joined the household. When he first moved in I had no issues with him. I went into CAS and updated all of his outfits a little bit and that worked fine. But after a week or two in game I tried to add additional outfits and his change outfits menu seems to be broken now. Whenever I add a new outfit, like an additional party or sleep outfit, the thumbnail shows up as a duplicate of his everyday outfit, and if I try to change into it, he stays in whatever outfit he's currently in. Also, all of the original thumbnails have reverted back to what they were before I updated them, and when I try to change him into those outfits he changes into that old version, even though in CAS they're still updated. For awhile he would still change into the outfits I made autonomously, like when he went to bed he'd change into the sleep outfit I made, but even that has stopped happening. I've tried everything I can think of including reseting him, getting rid of my limited CC (he didn't have any), and clearing my cache. He's not an occult Sim or anything. I did try saving the household and downloading it to a new save file, and that did seem to resolve the issue, but I'd really rather not have to replace him in my main save and lose all my progress and relationships (he's currently working on the Friend of the World aspiration). Is there anything else I can try to fix him, or do I just need to accept that he's broken and won't wear the clothes I want?