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You should have some options on dressers to plan outfits. If you don't, then you need to go buy some. Hop in the car, go to a community lot that sells clothing, pick out some, and take it home. Then you should be able to do it. Make sure if you get a top or bottom everyday that you get a top AND bottom - you may have problems with the plan outfit options if you have one but not the other.
my simblr (sometimes nsfw)
“Dude, suckin’ at something is the first step to being sorta good at something.”
Panquecas, panquecas e mais panquecas.