David Clark, headmaster of Art in the Algarve (Olhau, Portugal), kindly agreed to serve as a model while I was at his school for a portrait class.

The initial sketch is all about detailed measurements. 

I lay a light wash over the sketch to keep the pencil from smearing into the paint. Then I begin with the undercoat on the face.

I keep working up to lighter areas of the face and laying in the darker parts of the shirt.

I work on the shirt and glasses for a while and spend a lot of time thinking about how to finish the face.

Getting there, but something is bothering me about the eyes. They look jolly but lack character. The thing I like about David's eyes (and character) is the slightly piratical touch.

I add the tiniest white highlights above the eyes and it changes everything.

The Headmaster    
Oil on canvas. 21 x 18 inches (54 x 45 cm). $700.