PORTRAIT AS SYMBOL. Significant environments, objects, and expression are important tools we can use to convey something about a person, and make a portrait that stands as a symbol of who they are. I like to collaborate with people, and help them determine how to express something about themselves. Most of us also want to "look good" in a portrait, but we can say more about ourselves than that!
BLACK AND WHITE OR COLOR? Color provides more information, but it can also be a distraction. Black and white portraits have a timeless look, and focus our attention on expression, posture, and the graphical qualities of the image. I find it easier to make an expressive black and white portrait, and that color is more descriptive. Mary's attitude is what her portrait is all about, while it was important to Peter that his favorite old shirt be captured. If Robert's paintings had been in color, they would have distracted us from what the image is about, which is him, and his attitude about the paintings. The colorful flowers and books surrounding Sallie support her beautiful smile and pleasant environment, but this image would have also worked well in black and white.
HOW WILL IT BE USED? Desktop photo or wall sized portrait? Advertisement, book jacket, or brochure? Family heirloom or holiday card? An executive portrait usually shows a person in an environment related to the job, but a personal portrait of the same person might show a golfer, sailor, or musician. An editorial portrait accompanying a magazine article might not be the same one a scientist would want to give to a spouse or lover.
DRESS. Many photographers urge their clients to dress casually, but it all depends on what side of ourselves we want to show. Golf shirt, swimsuit, and black tie can all have their place. What kind of statement do you want to make?
WORKING TOGETHER. The best portraits are a collaboration between sitter and photographer. Great portraits are everywhere...look at the people pictures in the magazines and newspapers you read. Business Week, The New Yorker, Vanity Fair, and Sports Illustrated all have great photos of people, and you can follow my links for some real classics. It won't work to say "please do this one for me" but talking about what you liked about portraits you've seen is a good way to begin creating one together.