Tamur asked if I'd describe my work process, so here goes:
I only kept one file for each picture (given that each portrait is relatively simple - for more complex pictures I do save various stages), which I over-wrote at the end of each session, so I'm afraid I don't have any step-by-step pics to show.
As far as ideas go, I get inspiration from all over the place - books with good descriptions, films, TV, paintings and drawings, people in the street - there's no end of material to draw on, and, generally, any interesting expression, angle, gesture, set of features or lighting setup is worth noting.
Basically, though, it's a similar process to wraithdt's (I also use Photoshop and a graphics tablet): I start with a pencil sketch, which I scan (although the 2nd and 3rd pics were sketched in Photoshop). Either way, the sketch is on a separate layer is set to 'Multiply', so I can paint underneath without ruining the sketch (I used a canvas size of 1500 x 2250 pixels, so I could paint freely enough without having to worry about individual pixels, and also so it'd size down to 50x75 perfectly). By now I've a pretty good idea of what colours I'm going to use, and I've determined the light direction and intensity in the sketch. I then rough in the background, as it's always easier working the background first (with regards to figuring out exactly how the subject will be lit). I create a separate layer for the actual figure, simply so I can re-shape any edges and still keep a clear divide between background and portrait.
To begin the portrait, I spend a while blocking in the basic colours, not bothering with any detail until all the tones and colours feel about right. After that, it's just a matter of working a bit more detail into the picture until it feels 'done' (given that the avatar itself will only be 50 x 75). I'm also constantly checking what it looks at a smaller size, to make sure it minimises well.
Sorry if that was a bit long-winded, and I hope that, in the absence of pictures, the description is worth something!
Mid.
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