Here's the state of the question:
All agree that when it's worn to entice men other than one's husband to impurity, makeup constitutes mortal sin. Makeup worn out of vanity constitutes mortal sin, but more than likely it's the vanity itself that's sinful, not so much the makeup. Excessive amounts of makeup, when not conducive to sins again purity (some women look downright ridiculous), are venial sins because they distort nature.
Now, Cardinal Cajetan and the Salamancans hold that there's nothing inherently wrong with makeup in so far as it's an improvement on nature and a way to approach a natural ideal. I am a subscriber to this line of thought.
St. Alphonsus, quoting St. Thomas, who in turn quotes St. Augustine, say that makeup is never not sinful. They list the criteria that would make it mortal, but then say that it's always at least venial because it's "deceptive". But here's the point they're making that appears to have been missed here. They hold that deception is wrong because "men do not wish to be deceived". They say that women who dress extravagantly do not sin because they do so at the behest of and with the permission of men. But they assume that no men approve of makeup. But in today's society, very few men disapprove of makeup, and it's become a common cultural norm to wear it. Now, quite a few of these theologians hold that it's even OK for a woman to bare the upper part of her breast if it has become custom. [This opinion appears to have since been rejected by the directives of the Holy Office under Pius XI, which list objective criteria for immodest dress that do not appear to be relative to cultural norms.] In any case, however, some men not only do not disapprove of makeup but even prefer that women wear it. No one is really deceived by makeup, since it's so common and not in the least unexpected by men. It's not like men are going around saying, "Hmmm, she's obviously naturally this pretty" but then later are surprised by the lack of makeup. They know that makeup could be in play and could have improved upon the woman's natural appearance. It's up to them to investigate if they think it would make that much of a difference to a shallow man who might reject a woman whom he otherwise is attracted to ... all because of makeup.
In any case, the reason they give for why makeup is always sinful has to do with the assumed disapproval of men. I hold that since men no longer disapprove, then it's no longer inherently a venial sin to wear makeup. Now if a woman wears makeup against the wishes of her husband, that would be a sin of disobedience.
Even unmarried women who wear makeup simply to reduce the impediment of the bad "first impression" due to lack of makeup ... and men indeed tend to gravitate more towards the women who do wear it rather than those with virtue and spiritual beauty ... in order that a man might get to know them for who they really are, I feel that they commit no sin at all. Certainly, some men may well not "look at them twice" if they are not wearing makeup, but then might get to know them and see the beauty inside, and care less and less as time goes on about what she looks like without makeup ... once they get past those superficial considerations.