The only way I know is per category. That’s how I do it. So for example I pick an everyday makeup look and hairdo, apply it to outfit number 1 in the everyday category and then it will remain on outfits 2-5. Then I pick a formal look and repeat. If I want to change the hair on an outfit it’s easy enough and the makeup is done. But, by that same token I can change all or part of the makeup on a specific outfit too. Generally though, I just pick the one makeup look and stick with it for the entire category, and mostly just change the hairstyle here and there. I only give the sims I play most multiple outfits per category. Townies and bit players generally just get the styled look treatment.
ETA: that being said though, a system like I have heard other people mentioning where we can have it move from category to category should be possible because I have noticed that when I open the hot and cold weather tabs to style those outfits my sim is always already wearing their everyday hair and makeup.
