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I used Art Set to draw and paint over the photo, then processed in iColorama to produce four versions. Art Set gives a hand painted look, while iColorama post-processing gives a finished caricature-like look.
I used this photo from the Sktchy app. Sktchy photos are small, so I upsized it twice using BigPhoto.
In iColorama, I used Adjust/Tonelab preset 4 for tonal separation, which pulled out the shadings and highlights in her hair and gave more dimension to her face. Then I used Style/Simplify preset 17 at medium opacity to soften some of the roughness that the Tonelab step revealed in the image.
The reflection in her glasses is uninteresting. I will use this photo from Pixabay, a source of copyright-free images, to blend into her glasses, to create a new reflection.
In iColorama, I used Effect/Blend twice, once for each glasses lens. Each time, I blended the Pixabay photo over the woman, resizing and positioning where I wanted it, and using an inverted brush mask, I painted the new reflection in the lens.
Now I opened the image in the ArtSet app. I painted her with oil pastels, using the color picker to match the color of the pastel with each section of the image I was painting.
Still in ArtSet, I drew in some lines using a thin paint marker, again using the color picker to match the color of the marker to each area I was drawing or to another color in the image.
Still in ArtSet, I used the sandpaper smudge tool to smudge each individual area of the image.
In iColorama, I used Form/Crop to crop a bit from the bottom of the canvas.
I used Style/Simplify at medium opacity to soften the reflections in the glasses, to give them a texture more like the rest of the image.
I increased lightness using Adjust/Exposure, and I increased contrast in Adjust/Levels.
I used Adjust/Tonelab preset 3 for more color.
I used Adjust/Tonelab preset 1 for more lightness.
I used Tone/Duotone in Lighten mode, at low opacity, to tone the shadows.
For a second version, I applied Style/Flat preset 24 at medium opacity. This is version 2.
Now for a third version. Starting with Version 1, I used Style/Simplify preset 17 at medium opacity to smooth the image, and then Adjust/Levels for a bit more contrast to adjust for the contrast lost in the smoothing step.
I used Style/Flow preset 1, which smoothes out all the lines in the image for a cartoonish look. I applied Effect/Denoise preset 4 twice, to reduce the jagginess in the lines that is produced by the Flow step. Then I applied Effect/Raise preset 1 at low opacity for definition.
I used Form/Warp for a different look. This is version 3.
Now for a fourth version. Starting with Version 1, I applied Style/Flat 18 at medium opacity, experimenting with all the sliders.
I used Adjust/Tonelab preset 4 at low opacity for tonal separation, Adjust/High preset 1 at medium opacity to bring out the highlights, and Adjust/Levels to lighten the image a bit.
I used Style/Flow preset 1, then Effect/Denoise preset 4, before Effect/Raise preset 1 at low opacity.
I used Form/Warp for a different look. This is version 4.
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