Step 1 Using a photo reference, I make a clean line drawing, focusing mainly on the large shapes with similar values (His hair/beard/skin/large sections of similar colored clothing. Note, ignore the small details and focusing mainly on the overall shape.
Step 2 I throw down the main colors using a hard round brush and I like to use the darker values and build up. Then I merge the line drawing and the main color values into one layer.
Step 3 I refine and shape the large sections using a soft brush. I try imagine the values the light casts on the shapes. For instance, her dimple on the right, how would light effect that area? I used a photo as a reference.
Step 4 The details. This is probably the best part. I shrink my brush down and zoom in very close to capture the small creases in the face and clothing.
Step 5 Looking for small errors I glanced over and cleaning them up.
An afterthought, I have some sloppiness in there which probably could have been avoided with some masks. =]
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