We are not called to be mimics of the Blessed Mother, dressing as would be appropriate for a first-century Palestinian peasant woman (e.g., long veils, skirts to the floor, sandals). We are called to imitate the Blessed Mother in her virtues. In terms of modesty, that might mean dressing in a way that is appropriate to one’s culture and circumstances, not drawing undue attention to oneself either in one’s dress or undress, remaining circumspect about one’s own choices, and not denouncing the reasonable choices of others.
Overall, I agree with this article of Michelle Arnold. However, what tends to happen in discussions about modesty is that those on one side of the debate tend to present a caricature of the other side or generalize too much about the habits of the other side. In particular, I disagree with her remark about Fatima. I believe it is pretty clear what fashions Our Lady was referring to: the ones that lead many souls to hell. Enough said.
But I believe she is spot on with the last sentence in the quote. Modesty is both objective and subjective: it has to do both with the manner of dress and behavior of the one who is looked at, and the internal dispositions of the one who looks (or doesn’t look).
It seems to me that Christopher West, Fr. Thomas Loya, et al. place all the emphasis on the internal subjective dispositions of beholder. Many of those on the other side focus almost exclusively on objective norms of modest dress.
Objective norms are useful up to a point. But they can become counterproductive when they no longer help to form the conscience and begin to supplant the free use of good judgment, or when they facilitate zealotry, hypocrisy and rash judgment in regard to those who “don’t measure up.”
I believe the use of dress codes, in schools for example, are a slightly different question, because of the need for good order, for the students to have clarity of what is expected of them, and because of certain “political” and disciplinary issues.
Modesty is best taught in the context of general catechesis and spiritual formation. It is part of the life of virtue. I find where this is done, the standard of modesty goes up without too much scrupulosity or lack of charity.
And I think, ultimately, this is Michelle Arnold’s point. It is true devotion to Mary that will bring about Mary-like behavior. In the first place this is an interior change, and depends on a personal encounter with Our Lady for which no set of rules will substitute. In the end one must dress themselves. It is no one else’s responsibility and the choices involved here have to proceed from a heart which is modest.
Frankly, I believe one may find at times a modest bearing that may or not measure up to all the rules because there is real virtue present, and on the other hand, you can have rule perfection without deep virtue. It is interior union with Our Lady that helps us to make better judgments freely out of love for God. When that happens the outside will match the inside.