Ideas
I've noticed this happening to me as well. Say my sim is wearing their everyday, but then i change to cold weather wear and travel, and when the lot i traveled to have loaded, my sim is shown in their last outfit (everyday for example) - but when i click ''change outfit'', it says that they're wearing the cold weather wear, so it seems to me that it's some sort of weird and annoying visual glitch. It is really annoying. I do wish the sims also automatically changed into their everyday outfit whenever they come inside, and not run around in their cold weather outfits when it's actually warm inside. It is tedious to keep changing them every single time, but i guess that's a whole other debate.
Either way, this visual glitch thing started happening to me after the latest update/patch.