Decide if you want the person to be male or female. Male portraits tend to have stronger shadows, which may or may not be easier for you. Female portraits tend to have longer hair, and some people find a lot of hair boring and/or difficult to draw. Decide if you want the person to be younger or older. Older faces can be more interesting, yet more challenging, because of the extra lines and texture, but they can also convey the most emotion. Very little children are easier to draw, but may be harder if you’re used to drawing adults.
Go in further and draw the outlines of the general facial features, such as the eyes, some lines of the nose, inside of the ear, and lips, but don’t shadow anything in.
You can go back later and add details that can’t be seen in your reference photo if you don’t want your portrait to be an exact replica.
Determine the lightest and darkest parts of the person’s face. If you want your portrait to look 3-dimensional and dramatic, make the lightest parts as white as possible (with your hardest/finest pencil) and make the darkest parts and black as possible (with your boldest pencil).
Don’t forget that part of drawing a good portrait is capturing the uniqueness and expression of your subject. If your subject has a larger-than-average nose, don’t try to make it slimmer. Or, if their eyebrows are wispier, don’t try to darken them. A portrait should look like a real person, not an ideal.
