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She has been troubling me for quite some time.

I have struggled with her features and expression, in a way not too dissimilar to how we struggle against ourselves, until I felt I knew her well. I could well be mistaken.

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Photoshop, Painter

No direct reference, just looking at and impressing features, textures, lighting, both from pictures and from life.

Closeup:




Steps + brushes used:



Brushes:

In almost all cases, I set the brush's opacity to 100% and turn on 'Other Dynamics' setting Opacity and Flow to Pen Pressure (brush #1). So from then on I control opacity with how hard I press my stylus. In detailing, I turn on 'Shape Dynamics' (and turn off Other Dynamics), to achieve stark, refined strokes (brush #2). I use this for hair, details around the eyes, and the chain. Specifically for the hair and more subtle detailing, I will turn on both size and other dynamics (brush #3).
Textured brushes are very useful. I didn't go overboard here, but I used #4  (from a pack by concept-on-mac) for the background, #5 for speckling the face, creating pores so as to make the skin look less plastic (a common mishap with digital), and #6, very sparingly, for some areas on the hair and for smooth colour blending on the face.

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