April,
Here's a few thoughts ...
I like to move the drape/background as far back as I can get it from the subject. This keeps it from being too literal. I know you can paint it how ever you want, but I think you can engineer good shapes back there that can be rather inspirational. You can pin your material such that it can offer folds which end up being nice shapes (not literally material) of light an dark.
Also, if you are using a zoom lens, keep yourself out on the 80mm+ end if you can. Move your tripod up and back instead of altering the zoom. Be conscious that you are not down in the lower end of the range.
I also like to have people sit in a chair or bar stool instead of just standing in front of the camera. This gives the opportunity for more compositional variation. The knee can come up, the elbo can go to the knee, the hand to the face. Also, twisting the shoulders and the head can offer variation.
I'm not crazy about the shirts. I prefer a shirt with a standard collar and I really like a bow tie on a young boy. An interesting thing to add to the image and not very difficult to paint. I think it leaps the image forward a great deal and makes it more timeless.
Pay close attention to the light influences on the shadow side of the face. It's best to close off any light sources such as doors, windows etc. You need the dark as much as you need the light. It's a constant balancing between the two. I prefer a little more variance between the two than you show. If you spot meter the lit side of the face, as Allan suggests, it should take care of the exposure of the face and the rest will be acceptable.
Good luck
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Mike McCarty
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