Experimenting with drawing techniques

I began with this image of Trayvon Martin 

I attempted to trace it using Adobe Illustrator. I find it quite difficult using illustrator as the tools are quite fiddly. I used a different brush on his eyebrows in order to add texture. I also used different brushes to add shadows to his hoody.

I then experimented with drawing by hand. I just drew out a basic outline and a few shadows so that I could add colour digitally.

I used Photoshop to trace and colour the image. There were benefits and drawbacks of using this software. I found it much easier to use the magnetic lasso tool to select the outlines of the drawing. However this made the outlines look very jagged, whereas with Illustrator the lines are automatically smoothed out. On the plus side, I was able to give the image more depth by using the paintbrush tool to add shadows.

I think that with my next images I would like to use Illustrator to create the basic outlines or figures and then proceed to use Photoshop to add colour and details.