I love portraits! I usually try to do at least one form of a portrait with each grade level each year. Sometimes it doesn't completely work out for every grade level, but I try because I think they are wonderful snapshots of what the students were like in that moment. These ones are really neat because they are so expressive.
We started with learning about the super neat artworks of Guiseppe Arcimboldo. The kids were fascinated (I am too!!!!) by his portraits of people composed of many smaller objects. In his work, the small objects always have a theme or are related to the concept of the piece in some way.
These portraits started with classic facial proportioning guided drawing (I draw on the board, students draw on their papers). When it was time to do the hair, the students answered the question: What does your hair say about you? They drew all kinds of things and words in their hair and backgrounds. I encouraged them to make artwork unlike any one else's.
They traced their pencil drawing with Sharpies, and then colored with a selection of watercolor crayons, watercolor pencils, and washable markers. After they were done coloring with these mediums, they painted over their work with water. This helped to get rid of white spaces and to maybe mix colors if the students wanted. The only student that didn't paint with water made the portrait right below this paragraph. He absolutely loves markers and didn't have any white spaces to fix in the end!