My DD#1 sometimes wears shorts or leggings. It really depends on the situation. I told her Kindergarten teacher I would be putting a pair of shorts in her bookbag on the occasions we forget to make sure she's wearing pants or shorts for gym. Helena also insists on shorts if her shirt is shorter then her knees. She tends to be quite the tomboy so she has learned which outfits to put the shorts or legging on underneath for modesty.
Mom to 4 wonderful children
DS#1 7/96
DS#2 11/00
DD#1 11/03
DD#2 6/08