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How to choose a good portrait photo.

OK - one by one:

Don't use flash photography.
Unless you have studio equipment, reflecting umbrellas, slave flashes and all the other
gizmos, amature equipment produces an awful result. Usually, the flash unit is close to
the lens which makes the eye glow red, and puts a boring and predictable single-spot
reflection in the eyes. The front-on flash washes out all the features and skin texture to
leave a bland uninteresting picture.

Do use natural light.
Directional light that enters from the top left works well. We expect light to come from
this direction, and when a painting/drawing or even an abstract work of art is viewed,
we tend to 'read it' left to right. This is a cultural bias for those that read left to right,
and some cultures will prefer the light to come from top right. When the light comes
from below it tends to look like something from a horror movie or thriller. This is a mind
trick.

Let's assume that your subject is in a dim room with a bright light source coming from
the top left. This will produce a nice strong set of shadows that will define the features
well. If the light came from directly above, then it tends to give people a 'Hitler moustache"
shadow - even on women. In some cases the top-left directional lighting works well, but
it might help to stand your subject next to a reflective surface on their left (your right).
This will brighten up their left side with a diffuse less-strong light. Finally, some windows
or other bright scenes over to the back of you and to the right or left will make some
interesting reflections in the eyes.

Do use a tripod
When you are using natural light, it is not as strong as a fast bright flash so any movement
in the camera or the subject will cause camera-shake or motion blur. Sometimes motion
blur looks artistic, but camera shake almost always looks bad. Try to avoid both. Use a
tripod or a wall or some other handy solid support.

Take multiple photos
When you are trying to get good references for a portrait, and a live sitting is not possible,
then many photos give the artist more chance to capture the essence of the personality.
Take some smiling, frowning, laughing, and some with eyes wide open or close and so on.
Finally, take a few of the desired pose. The desired pose should be interesting. Rarely this
will be face on; mostly it will involve having the head at an angle. Sometimes, eyes are
closed or looking up or down. It depends on the effect that you are trying to get.

Focus on the eyes
Especially in low light, the camera has a limited depth of field. Under very low light conditions
it might not be possible to get all the the face from the tip of the nose to the sides of the ears
into perfect focus. If that is the case, then focus on the eyes. As long as the eyes are in focus
our perception is comfortable.

Consider using a hat
Sometimes your subject will squint because of incident light. In this case, a hat might help.
A hat may also provide an interesting prop. Straw hats and light colored hats can be quite
helpful. However, you need to be careful because the brim of the hat can mute all detail
over the eyes. In this case, try to find a way to get some light reflected under the brim.

Use a longer lens.
A lens 50 to 100mm focal length is considered best for portrait work. Short lenses distort
and long lenses compress the image in depth.