This is a portrait I painted a few weeks ago. At the start, I tried to choose a pose, a hairstyle and clothes which suited the model best, but ended up painting her looking like, well, what she normally looks like, (Rebecca is an undergraduate at Oxford) and wearing what she normally wears (jeans and pullover). This seemed to suit very well.
A lot of the time, people would like to have smiling portraits but as producing a natural smile for more than thirty seconds is actually quite tiring, I have never asked my models to smile for me – I once tried smiling for a self-portrait and it was painful work even after only an hour. Fortunately, Rebecca is the fairly relaxed sort and has a naturally happy looking face, so the hint of a smile is always there.