Personally, I think that a boy wearing shorts in a "dressier" type situation who is older than about six just makes me think of Little Lord Fauntleroy. It is cute, like at Easter, when a little boy wears dressy shorts, shirt, belt, maybe even a jacket, along with nice socks and shoes. I think that an older boy may well feel a little uncomfortable with that, and might prefer to wear khakis, which take some of the attention away from the legs/socks/shoes area and not make them seem so "little boy"ish. We have some nice, yet inexpensive, lightweight pants from LL Bean which my son wore to dinner. I think he looked neat and presentable and met the dress code, without any real expense or discomfort.