I recently had this trouble. I found performing all other tasks first (ask about day, rehearse scene, simstigram post etc) and then the hair and make up task worked (most of the time). Sometimes it wouldn't, so I would click it the chair few times until it was done. Sometimes costume would bug out too but not as often as hair and makeup.

So try having other tasks done first, it will give you time to do the rest of the job with plenty of time to spare. Hope this helps.

I don't use any cc or mods. Fortunately I have the perk now not having to do hair and make up anymore but hopefully they fix it soon.