Feels most comfortable bare-chested
Kim: I have read the posts directed towards whether it's good to paint a child bare-chested or not. I believe an artist should paint a portrait to portray the child. In your case, I do agree with the others that the child looks scary but that doesn't mean that you can't paint him bare-chested. If the child feels most comfortable shirtless then you could still do that. You just may want to pose him differently.
Wende Caporale, pastel portrait painter, coincidentally has a bare-chested boy printed in her portrait book. Her comments were "his parents and I posed him in several different shirts. But the most natural photos of him turned out to be when he was shirtless, because this his how he feels most comfortable. This highlighted his free-spirited personality and resulted in a striking portrait."
There is no set rules out there in what an artist can or cannot paint. I do admit I haven't seen too many bare-chested boys but as mentioned above if it's the child's personality...go for it!
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