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I have never painted a little girl in a long white dress. When advising parents about clothes (both as a painter and much earlier, when I did child photography) I always suggest timeless, classic clothes which are fairly loose and drape well. Sundresses, pinafores, jumpers, or other shortsleeved skirted clothing for girls, and loose shirts and shorts for boys, are what I prefer. If I'm doing a whole figure I often paint them barefoot. I try to avoid clothes that are too fussy and that draw attention from the subject's face and form. At times I'll even change the color or minimize the pattern to make a more pleasing painting; when I've explained my reasoning no one has ever had a problem with that. Many of my photos sessions do occur in the summer, which accounts for the briefer clothing, but I would be just as happy to paint a child (or adult) in velvet. I have painted kids (waist up) in sweaters as well, but as suggested, I don't want the portrait to look dated. I also try for classic hairstyles and in the past have waited for a boy's hair to grow in from a too severe cut before taking the reference photos.
The other day I saw a highschool yearbook from 1975, when long hair for boys was the rage, and I was amazed at how dated and unsavory those with the more extreme styles appeared! Another argument for going for the classic look.
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