Cartier-Bresson “Photography is an immediate reaction, drawing is a meditation.”
Cartier-Bresson, the famous photographer and one of the founders of Magnum Photos, associated with the “decisive moment” was passionate about drawing from life. But what about drawing or painting from photographs? Can it be a tool and still lead to a act of meditation, contemplation, reflection, and expression when the artist uses it as a starting point, a reference, and departs from it, ultimately? And doesn’t a photographic series lead us to the same place when it goes beyond the snapshot to become art?
Some basics about drawing features:
A speed drawing of a portrait, summing up drawing as a series of adjustments:
Drawings and portraits by Georges Seurat:
Here is an excellent glaze painting demo by Domenic Cretara, part 1-3 Look up all stages(-12) for the visuals and the advice as you work on your own. Since we are doing a monochromatic painting, we will not be galzing to full color as he does. But, you may return to your painting in the future to do so.
And here is an article and some of his work from the Triton Museum show in Santa Clara:
Another monochrome portrait painting tutorial:
Another monochromatic approach:
Whether considering the rub-out technique or considering the second portrait from your digital references you may want to consider Notan, the Japanese sense of dark/light balance in a composition;
And here is a mural which relies on notan in the portrait:
A resource with a variety of contemporary, stylized, historical examples and tips on portraits:
Portraits by Catherine Kehoe:
And finally, a look at the painting of Queen Elizabeth by Lucien Freud (a small painting on a big easel, like yours):
And the controversy it caused:
Or a comparison of 30 portraits of her: