I am sorry, I don't completely understand, could you give me more infromation so that I can help.
He might mean that he is better than what he seems to be.
Answer:
Yes, "They act as if we wore our skirts too short and invited trouble, presents an effective analogy.
Explanation:
The comment was made against Washingtonians. The analogy represents the difficulty for individuals who may have forgotten their status quo. The shortness of the skirt reflects the onerous and the encouraged difficulty represents their unpleasant memory about it.