some other possibilities
Helvetica, perhaps this information will lead to answers to some of your questions:
Tom Tadfor Little pointed out that the title "High Priestess" first appears (as "La grandpretresse") in the Grandpretre tarot, issued in France probably around 1800 and inspired by Court de Gebelin's book Le Monde Primitif, which launched the occult tarot revival. Before that, the card (when it is not replaced by a completely different subject) is invariably called the Papess (female pope): "la papessa" in Italian, "la papesse" in French. To read more of Little's study on the history of the Major Arcana, visit The Hermitage: A Tarot History Site.
So how did the Papess card turn into a high priestess? Again borrowing from Little: by the time of the Counter-Reformation, the female pope was often considered an inappropriate subject for the cards and was dropped from many decks, though not from the Tarot de Marseille which was the base for the occultist decks. Some insight into the transition can be gained by looking at a number of suggestions that have been offered as the source for the original 15th century image.
1. There was a custom of using female figures to depict institutions or abstractions, so a female pope might represent the papacy or the church at large. Kaplan, Vol 2, p 160, shows a reproduction of a painting by Vassari that celebrates the victory of Spain, Venice and the Papacy over the Turks. Here the Papacy is represented by a female Pope. However, if the Papess had been intended to represent such an abstraction, one would expect the card to be labelled “The Church."
2. Renaissance art also depicts the legendary Pope Joan. For example, she appears among the historical popes in the 15th century Cathedral of Sienna. Joan was an Englishwoman who allegedly entered a monastic order disguised as a man. She rose in prominence and was elected pope, only to have her secret revealed when she collapsed in childbirth during a procession. The legend was quite popular during the time of the invention of the tarot, and persisted for centuries. However, Pope Joan is ordinarily depicted as giving birth or holding her baby.
3. Gertrude Moakley (The Tarot Cards, 1966) has called attention to a small heretical sect, the Guglielmites, which was active in Milan about a century before the tarot cards were invented. They elected one of their members, Manfreda, as pope! Manfreda was a relation of the Visconti family who ruled Milan and commissioned the earliest surviving tarot cards. On that deck, the Papess is shown in the habit of the Umiliata, the order that Manfreda belonged to. However, beyond the deck specifically produced for the Visconti about 1450, the local Milanese phenomenon of Guglielmites is unlikely to be the source for the image on earlier decks, for example, the 1442 deck mentioned in an inventory of the Este estate in Ferrara.
4. Little ( The Hermitage: A Tarot History Site) develops the idea that the Papess did not represent an individual person so much as a dualistic principle to balance the male Pope card, just as the Empress forms the female dual of the Emperor. This dualism, evident in many of the Tarot trumps, may stem from Catharism, a popular dualist heresy that flourished in the city states of northern Italy.
As a public entity, Catharism was eradicated by the Inquisition by the middle of the 14th century (Lambert, M. 1998. The Cathars. Blackwell, Oxford) but dualistic concepts continued to influence Italian culture well into the 15th century and beyond. This explanation is appealing because it helps explain why the Papess evolved into the High Priestess even as its dual, the Pope, evolved into the Hierophant.
5. However, there are also hints that the Papess image was associated with a Pagan goddess/priestess from the beginning. For example, the Papess may represent Isis who was very much a part of Late Medieval and Renaissance thinking. Peter Comestor wrote an influential history of God's People in 1160 that discusses Isis as the inventor of letters and writing. Isis also appears as a complete chapter in the History of Jacopo da Bergamo (1483). And we should not forget Plutarch's influential work: "Isis and Osiris" from which we can get the modern associations with the crescent moon and water seen in the Waite-Smith deck.
An image of Isis appears in the Appartmento Borgia in the Vatican (Yates: Giordano Bruno, plate 5). She is seated on a throne between two pillars with a veil stretched between them and a book in her lap. There is also a Renaissance image of Isis with the orb and horn crown (Shumaker: Occult Sciences in the Renaissance, p 247).
6. There is a figure of the High Priestess of Venus in Leon Battista Alberti’s Hypnerotomachia Poliphili (1499). She appears in Chapter 31:
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http://mitpress.mit.edu/e-books/HP/hyp435.htm
There are also images at:
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http://mitpress.mit.edu/e-books/HP/hyp429.htm
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http://mitpress.mit.edu/e-books/HP/hyp431.htm
This image may be completely unrelated to the Tarot image but does suggest that the High Priestess of a pagan goddess was part and parcel of the Renaissance imagination.
7. The Papess image may also represent a Sibyl. The Sibyls were pagan prophetesses who were believed to have predicted the Virgin Birth and other aspects of Christianity. Although unfamiliar to us, the Sibyls were an important part of late medieval and Renaissance culture because of the Sibylline Books, the earliest dating back to the 4th century. Cohn (The Pursuit of the Millenium, Oxford University Press, 1970, p 33) points out that "uncanonical and unorthodox though they were, the Sibyllines had enormous influence - indeed save for the Bible and the works of the Fathers, they were probably the most influential writings known to medieval Europe.
They often dominated the pronouncements of dominant figures in the Church, monks and nuns such as St. Bernard and St. Hildgard whose counsel even popes and emperors regarded as divinely inspired...From the fourteenth century onward translations began to appear in the various European languages...these books were being read and studied everywhere."
Imagery derived from the books was widespread and therefore available to the illiterate. Finiguerra's "Picture Chronicle" ~1460 (99 images representing history) shows Sibyls. Phillippus de Barberiis "Opuscula" (1481) has illustrations of the 12 Sibylls. They are found on French Cathedrals of the period. The church of San Francesco di Rimini (~1450) has images of Sibyls as does the Cambio of Perugia and the study/library of Pope Julius II in the Vatican. They were common illustrations in prayer books (Books of Hours). Sibylls are in the pavement of the Sienna Cathedral. They were probably a part of the original floor plan (~1400) and were executed ~1480.
The easiest access to images of the Sibyls is in Levenson, Oberhuber and Sheehan Early Italian Engravings from the National Gallery of Art. There you will find, for example, the Sybil of Persia: seated, elaborate robe, book in her lap, face partially covered by a veil.