
This portrait is of three women representing three generations. I think I nailed the likeness of all three, but it's always nerve wracking to see if the client will like the work (he hasn't seen this yet.) I had to combine two photos to create the composition and I've only seen one of the subjects in person.
Painting faces is not as daunting as some would think. Each face has reference points that can be measured - space between the eyes, length of the face, length of the nose, width of the smile, etc. A projector is a great help in getting accurate mapping of the key points on a face. My projector is an inexpensive model that projects a pretty fuzzy image, but it is a huge time saver to be able to
sketch in the key points of the projected image.
Teeth can be a problem to portray and all these ladies have big, beautiful smiles. If you paint each tooth, it tends to look artificial, so I usually "suggest" teeth without painting them individually.
I love to paint people with glasses. They are a very important part of the "look" of a person who wears them. I like to tint the glass slightly blue or blue-green.