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I always recommend that my subjects wear solid (not busily patterned) clothes in classic styles that won't make the portrait seem out of date in a few years.
I usually paint kids and here's what I tell my clients: I might suggest khaki pants and a white button down shirt for a boy in an indoor portrait, or perhaps a light colored polo-type shirt with solid cotton shorts for outdoors. Little girls look great in white or simple solid-colored dresses, both indoors and out.
Things that I would recommend against would be clothing in a very strong color that might be overly dominant in the composition, or anything with strong stripes or other bold patterns. I would also not want to paint a portrait with a subject wearing a t-shirt with writing or other images on it.
In my portraits I try to aim for a classic and traditional feel, though not old fashioned. I usually suggest my clients have the subject of the portrait dress in a way that fits that concept.
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