"Hillary" illustration done on an iPad Pro using Adobe Illustrator Draw and an Apple Pencil. July 21st, 2016
Step 1 - First I do the main line drawing.
Step 2 - Then with my Illustrations where I use the technique, I add the cross-hatching to create the shadows and depth. Cross-hatching is a technique that has been around for centuries and centuries and something I practiced many, many times to get right. I do somewhat cheat with it since I also use color as using different colors makes it easier to also achieve the shadows and highlights I am going for.
Step 3 - I add the "main" colors which are usually just one solid color. I also almost always finalize the eyes as well early on, as I believe they are very important and set the tone of everything else.
Important Note - The Eyes and Lips are also on another Layer above everything else.
Step 4 - The final step, and the step that takes the most time usually, is I add additional shapes to make up the shadows and the highlights of the face. These subtle but important shapes wind up providing the definition for the face itself. I usually create several layers when doing this step. The shadows/darks are always on the bottom layer. I usually wind up with 3 to 4 layers. Shadows. Midtones. Lights.

Important Note - For the pieces I use cross hatching, as you will see in Step 3, the cross hatching starts to define the contours of the face even without putting an additional color. However I do add an additional color underneath the cross hatching as well especially if I want that area to be a "deep" shadow.

I then add a simple background to all of my illustrations. I keep the background very simple on purpose. It is the portrait itself I consider to be the main artwork. I also try to keep negative space and composition in mind overall as well.
I hope it helps some people out me sharing my process. I simplified it for the sake of the illustration, and quite often I will work with several layers at the same time to achieve one step. For example just the lineart, it was made up of 3 to 4 layers I eventually just combined to one layer.
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