I don't think changing outfits works unless you have a makeup predefined for the outfit you are telling that sim to change into. I actually prefer that changing outfit wouldn't change makeup because in real life if you simply change your clothes your makeup doesn't come off. However, that would be my personal preference.
I think in my game I don't get a change in makeup if I just click on the Sim and tell them to change outfits. For example, if my Sim is still in their sleep outfit and I have them put on makeup, then tell them to change to everyday outfit, they will still be wearing the makeup they just put on at the vanity, not the makeup that goes with the everyday outfit. But I'm not sure. I know that any action that automatically forces a change of clothes will remove the vanity makeup though (sleep, workout, jog, swim.)
I don't know what happens with parties or weddings. It would be awful if you had, say a bride, sit at the vanity and put on makeup, only to have her lose it at the altar when she spins into her wedding dress....
