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The fashion today is towards more naturalistic and less posed looking portraits. So if a prop is used it has to be done with care. If you sit and talk to someone how often do they hold something in their hands? This is the key. I think a dentist holding a drill for instance wouldn't go over too well (humor!?!). A child holding a stuffed animal is another story. Glasses work because this is a natural occurance during conversations. basically there are no formulas. You have to balance the naturalism with a good composition, no easy task.
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