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Ding ding ding, someone who knows what they’re talking about has written in! On the subject of paintings of the visibly pregnant Virgin Mary, Asa says:
I’m a historian of medieval art, so I was delighted to hear the subject come up in AMT328. You were talking about the lack of medieval images of Mary pregnant. There are, though, TONS of these. The trouble is that you need to know the right term to search. “The Visitation” is the term for a scene wherein Mary and her cousin Elizabeth get together to celebrate their simultaneous pregnancies — Mary pregnant with Jesus (of course) and Elizabeth a bit further along in her pregnancy with John the Baptist.
The associated feast was made church policy in 1389, which might be why there are more images starting in the 15th century, but there are also just more of all kinds of images starting in the 15th century. The Knight’s Templar theory you found is almost certainly not right. Pretty much everything said about the Templars is tinged with Dan Brown conspiracy theories.
I bet there are older ones, but that’s surely more than you wanted, anyway.
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