Normally I post portraits in the 100 drawings series in sets, but this one drove me so crazy that it warrants its own separate page. 

Caleb is the printmaking teacher at The Putney School Summer Programs, and we work in neighboring studios. I knew that I wanted to draw him in his signature suspenders or overalls, but every time I saw him in either of these he was wearing a plaid shirt. I hate drawing plaid. I hate it so much that I'd sworn off of drawing it forever. However, he just didn't look like himself otherwise so I made one last exception. One that I would come to regret.
I tried to keep it simple, but I just couldn't do it. His shirt had a ton of different colors, so it didn't look right without at least nine different shades of grey, all of which needed to be drawn in little parallel lines.
This made the drawing super complex. So complex, in fact, that my iPad couldn't handle it. I eventually hit a point where three out of every five pencil strokes wouldn't even register unless I drew at a snail's pace. Seriously, look at this thing in outline mode:
There were a few times when I considered just throwing it out the window. I actually had nightmares about plaid for the last few days worth of drawing. It was worth it though. I always congratulate my students when they make something complex enough to cause their tools to lag. Hooray for testing the limits. 

Still, no more plaid though. Never again. 
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