Some time ago I promised that I would research veiling customs during the time that St Paul lived, as I wasn't convinced that women always wore headcoverings outside the house. I've finally gotten around to doing some research, which I'll be presenting below.
Often arguments around whether women should cover their heads in church dismiss it as a custom that was prevalent in society as a whole then but isn't relevant now. Some comment that since women always covered their heads outside the house in earlier times but don't do so now the practise is now archaic. The question is, are these conclusions supported by the evidence?
(Please note that I am not arguing that there's a canonical requirement for veiling. I think people such as Fr Z, canon lawyer Edward Peters, and Jimmy Akin have made it clear that there is no canonical requirement to veil. I'm only looking at the cultural practises at the time.)
I'd first like to address the Scripture in question. Here's 1 Corinthians 11:3-16 from the Jerusalem Bible:
3 But I should like you to understand that the head of every man is Christ, the head of woman is man, and the head of Christ is God.
4 For any man to pray or to prophesy with his head covered shows disrespect for his head.
5 And for a woman to pray or prophesy with her head uncovered shows disrespect for her head; it is exactly the same as if she had her hair shaved off.
6 Indeed, if a woman does go without a veil, she should have her hair cut off too; but if it is a shameful thing for a woman to have her hair cut off or shaved off, then she should wear a veil.
7 But for a man it is not right to have his head covered, since he is the image of God and reflects God's glory; but woman is the reflection of man's glory.
8 For man did not come from woman; no, woman came from man;
9 nor was man created for the sake of woman, but woman for the sake of man:
10 and this is why it is right for a woman to wear on her head a sign of the authority over her, because of the angels.
11 However, in the Lord, though woman is nothing without man, man is nothing without woman;
12 and though woman came from man, so does every man come from a woman, and everything comes from God.
13 Decide for yourselves: does it seem fitting that a woman should pray to God without a veil?
14 Does not nature itself teach you that if a man has long hair, it is a disgrace to him,
15 but when a woman has long hair, it is her glory? After all, her hair was given to her to be a covering.
16 If anyone wants to be contentious, I say that we have no such custom, nor do any of the churches of God.
So we see here that St Paul says men should have their heads uncovered for religious gatherings, and women – all women, regardless of social class or marital status – should cover their heads. We still see that men uncover their heads for Mass (this is perhaps more obvious with a Bishop, since he removes his mitre or zucchetto for parts of the Mass), and some women cover their heads. The question, though, is the practise at the time that St Paul was writing.
Outside of religious observances, though, what was the Roman practise? I found Kelly Olson's book to be quite helpful. She focuses more on Rome itself and not the provinces, but the information is still valuable. In the Roman Empire, the prescription was that matrons wore a palla, a long garment that covered most of the body and would be pulled up over the head when out of the house. This only applied to matrons, though, and not unmarried women. Further, it doesn't seem to have applied to married women of the lower classes or to slaves, for the palla would not have been a practical garment if one had to do physical labour. St Paul, however, does not make a distinction between marital status or social class in his command.
Greek dress also dictated that women wear a himation which could cover the head. However, it did not just cover the head, but was more akin to a burka, covering the entire body except for the face. I have also found that Lloyd Llewellyn-Jones' research indicates that Greek women commonly went in public fully veiled, with head and face covered (the source is listed below; I was unable to get the book and so had to rely on the website listed that gave me that source).
St Paul, however, does not make a distinction between marital status or social class in his command. On the contrary, St Paul remarks in places about how all are equal in Christ, so having different rules for citizens and slaves would not be in keeping with that, it seems. St Paul also does not advocate for the more extreme veiling of Greek women which covered the woman completely. He does not seem to be succumbing to cultural mores since he speaks of this as a universal tradition throughout the Church at the time, and it doesn't have absolute parallels in the surrounding cultures in the way it is practised.
My conclusion, then, is that St Paul is not just upholding the cultural mores of the time. He in fact seems to deviate from the cultural prescriptions in many regards by not having different rules based upon social class and marital status. It later becomes the norm that women cover their heads everywhere (St John Chyrosostom speaks of this being the case), but it likely varied from area to area, especially as the Christians went to the farther reaches of the Roman Empire and beyond. So I'm not convinced that one can say that veiling has lost its meaning now that women don't cover their heads any time they are out of the house, since it appears that they did not always cover their heads when leaving the house in St Paul's time, either. Again, I'm not arguing that veiling is mandatory; the Church doesn't say that it is and I will not argue otherwise. I just wanted to research the historical practise a bit.
Llewellyn-Jones, Lloyd (Edt), "Aphrodites Tortoise : The Veiled Woman of Ancient Greece", Classical Press of Wales, December 2002
Cairns, Douglas L. “The meaning of the veil in ancient Greek culture”, Women's Dress in the Ancient Greek World, ed. Lloyd Llewellyn-Jones, p73-94.
Olson, Kelly. Dress and the Roman Woman: Self-Presentation and Society.