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Michele, WOW! All this time I've been imagining what this portrait must look like, and I had some hazy idea, but nothing could have prepared me for the reality. It's very exciting to see it. One thing I noticed immediately: the proportions of the canvas are elegant.
It's very interesting how his relaxed leaning pose complements certain features that are rather tense (hands, mouth, jaw). You seem to have pared down his appearance, and maybe even his character, to a few important essentials. Everything that is there tells the viewer something important. His eyes tell you he doesn't miss much. The indentation at the corner of his mouth and cheeks indicate a sense of humor. (At least this is how I'm reading it!)
I also love the way that the sweeping line of the chair is strong enough to continue the curve of his posture down through the whole bottom third of the painting,
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