It's easier to caricature someone who isn't a professional model.
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Trying to figure out how the body works under all those lumpy clothes is a problem.
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More lumpy clothes but a good head to draw.
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These caricatures are still conservative because I am drawing the people for the first time and only from one angle.
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Whoops, I see I got lazy and drew at an angle instead of looking straight at the paper. That makes my drawings look skewed.
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Here, I cheated and skewed it back in photoshop.