here's the basic head shape, drawn right over the photo: now i block in the basic shapes i see in the photo: the hat, the scarf, the hair: i lay in the abstraction lines of the face, focusing on the ones i see in the photo, given that high-contrast light and his face type and his age: i put in the shadow pattern, so that i have a decent idea of where the darkest and lightest values are.... i'm not thinking about details at all, just about things like where his tooth cylinder is, how his cheek muscles fit into his jaw, etc. although i'm doing this paint-over in photoshop, i turned off the layer with the original photo a while ago and have just been using what little i know of the head anatomy to make my drawing: now i go in and work out some details, like the left side of his head (our left when looking at it), his hair, how to show that there's a scarf without drawing every single little fibre, fixing his hat, showing the texture of the hat without going crazy drawing to draw fluffy felt, etc. etc. and because it's now been 20 minutes, and i still have to write this post and upload the photos, i call it good enough for now.... go look at and memorize the anatomy and perspective books ron listed: andrew loomis' out-of-print bibles of drawing Anatomy Bridgeman's Complete Guide to Drawing from Life Stephen Peck-Atlas of Human Anatomy for the Artist John Vanderpoel-The Human Figure Fritz Schider-An Atlas of Anatomy For Artists Perspective Dora Miriam Norton-Freehand Perspective and Sketching Arthur Guptill-Sketching as a Hobby Guptill-Sketching and Rendering in Pencil Ernest Watson-Creative Perspective for Artists and Illustrators practice drawing from these.