This is less of a question and more of a point to ponder.
A recent post regarding da Vinci's "the Last Supper" starting me think about the way Leonardo sometimes portray's males. After it was renovated, it became apparent that da Vinci's original depiction of the figure sitting to the left of Jesus (as we look at the painting) was originally very feminine looking. This of course became popularised in Dan Brown's Da Vinci Code, where it was calimed that it was actually a depcition of Mary Magdalen.
But it seems that Leonardo was interested in painting effeminate men. His painting of John the Baptist is very feminine, and looks very much like a woman. The basis for that painting seems to be sketch he did entitled "Angel in the Flesh", where a figure is clearly depicted with both male and female characteristics. If you haven't seen these I suggest you look them up on the Internet. Here are a couple of links.
Leonardo seems to be into ambiguity. The famous enigmatic smile of the Mono Lisa. And the background of the Mono Lisa offers two seperate possibilities. The view to the right has a higher horizon, which makes the figure look smaller; while the one on the left has a lower horizon wheich makes the figure llook taller. The horizons do not match.
There is a theory that the Mono Lisa is a self-portrait of Leonardo da Vinci, advocated by Dr Lillian Schwartz. It would mean that Leonardo was quite effeminate looking, and played on this by creating a femalwe portrait of of his own.
I work with Photoshop and I decided to add some hair and a beard to the the famous painting. In an attempt to break the familiarity the public have with the Mono Lisa, I flipped the face horizontally, blurred away the cracks in the oil paint and alted the colour balance. No other changes have been made to the face.
All I did after that was to create a montage of hair and a bit of stubble and added these as an overlay to the face.
Just think, we might be looking at a young Leonardo da Vinci when we look at this. I hope you find this as interesting as I do.