My client gave me close up head shots, along with information about the digital caricature I was about to create for her.
Scene: Criminal lawyer, also runner, with shirt and silver pen saying “The Great…”
Sometimes, I draw straight from my Cintiq with photo open next to drawing, but at times, I will sketch on paper, then scan and trace, which is what I did here.

First step, a rough pencil of head, then body.

Scan and trace in Photoshop. I zoom up on my linework to make sure they are clean and not rough sketchy lines. Later, I will work on thicker lines for shadows.

I duplicate the layer with my black line work and set layer to multiply and then color.
I then merge layers after I color.

I started to add the background scene of the city and courthouse with sketching in Photoshop, fixing line work at close range, then color.

I added color shadows and other small touch ups with the details given to me about the scene (burglar, paper and writing).
I try my best to balance the drawing and keep a good composition.

Finished! Wah-lah!

This is one of many ways I do my studio digital. Other times, I use Painter and patch up with Photoshop. This one I did all design in Photoshop CS3.