Can you please explain how the modest way we are told to dress effects us and our level of observance?
This is a deep question, which I will begin to explore with you. But, like many deep questions, it is one that will only understand more fully as you mature and experience more of life.
Let’s start with a thought from the Vilna Gaon. The Vilna Gaon teaches that character traits are the clothes of the soul. Just as the physical clothes that we wear project the image of ourselves that we wish to display to the world, so too, the character traits that we display in our interpersonal relationships project the nature of our unique souls (Even Sheleima 1:1).
The Sefer Hachinuch (Mitzvah 99) notes that this works from the outside-in as well. When we force ourselves to express our character traits in a more refined way with others, we feel a change happening inside also. Our souls are touched by our actions. Similarly, the clothes that we wear affect our self-image. Basically, it’s all a two-way street.
I’m going to quote now from a fascinating book on this subject by Gila Manolson, called Outside/Inside (Targum Press – I highly recommend this book to anyone who truly wants to understand the Torah’s laws of dress). Mrs. Manolson writes that the Torah fashion ideal “is to transform the outside layers of yourself into an expression of your inside” (p. 24). This is not merely for the benefit of others, Mrs. Manolson informs us (restating the idea of the Sefer Hachinuch that we mentioned above): “What we often fail to realize is that the message of clothing is directed not only outward, to others, but also inward. What you wear powerfully affects how you see yourself” (p. 28).
Indeed, the main theme throughout Mrs. Manolson’s book is that Torah standards of attire are not merely dress codes. The Torah’s primary concern with externals (like clothing) is always how it affects our internal world. The Torah wants us to reflect on our clothing in order to, in turn, reflect on who we really are inside. What image do I project to others? Is this really me? And if not, then who am I?
As Mrs. Manolson asserts later on: “Other pluses notwithstanding, the fundamental purpose of tzniut (modesty) remains the cultivation of a deeply rooted, internal self-image� (p. 58).
Our clothes should be a reflection of our inner identities as much as our character traits reflect the nature of our souls.
I admit, it is more challenging for us to shop for clothes this way. But at least we’ll never have to worry about being out of style.