I'm convinced that any small child old enough to pick out his or her own clothes should wear a sign reading "I Dressed Myself Today." This way parents can't be blamed for the interesting combinations that can result.
A friend and I both have seven-year-olds with the same strange wardrobe habit. Her daughter and my son both believe that in order to "match," they must wear the same color from head to toe. So you might run into her little girl wearing a pink polka-dot top, pink plaid pants, and pink striped socks. It's all pink, so it matches. Similarly, my son thinks that he should only wear blue t-shirts with blue jeans. Red shirts need not apply. (Fortunately, he wears a uniform to school, so I don't have to police his "matching" decisions all the time.)
Recently I attended a funeral for a good friend's father. His youngest granddaughter is five years old, and her mom had a hard time finding an appropriate dress for the little girl to wear to the funeral. She finally found a long black velveteen dress with a butterfly pattern. That worked fine. But this little girl has her own sense of style. Despite the fact that she owns very nice black Mary Jane shoes, she chose to wear her "Ruby Slippers" to the funeral--as well as purple tights with big pink flowers on them. She accessorized with a long strand of play-jewelry pearls.
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