If I understand the question correctly, it seems like the main complaint here is “why can’t I just wear the clothes I feel good in” like everyone in general society wearing the clothes they choose, and instead must be restricted by a Halachic dress-code?
I think that we are making a critical mistake when we assume that all others in society are choosing their clothing freely and are happy with it.
And that is an erroneous assumption. It’s wrong because it’s evident that even in non-Jewish culture, there’s a certain level of expectation, a certain level of cultural pressure. It’s not uncommon to hear a woman or man complain about the way she is expected to dress for certain events or in specific environments, if not for the societal pressure, she might be much more comfortable wearing something different.
So let’s step back a moment and try to understand what will truly make us feel good. If it’s fitting into the culture, which can be stifling as much as “religion,” then maybe we should take a look at what’s most natural to us.
Before the Cheit Eitz Hadas, human beings had no shame to conduct their lives with no clothing at all, they were blissfully unaware of their nakedness. Only after the sin did Adam and Chava become conscious of it and began to look for clothing.
Hashem created in our human nature a need for privacy, a feeling of self-worth and self-esteem that stands regardless of the judgment of others. If we try to erase that privacy through the opinion of others, we will not feel good, we will only be going against our inherent nature, and will end up feeling miserable about ourselves.
Now there is a culture that seeks to push the boundaries continually, play with the rules, and encourage you to “fit in” to what “everyone” is up to. But that culture goes against human nature, it tries to fight it and tell you that it is what will make you feel good, but it won’t, it will just pull you further away from yourself and from your nature.
And there is the Torah culture, Halacha, which embraces human nature, it’s needs and feelings. It recognizes what we genuinely care about, and creates standards of dress that encourages the decency that we all deserve.
If we look at the big picture, we see that the Torah guidelines are not just a set of rules, but they are trying to teach us the best way to feel good about ourselves, responding to our dignity and decency, how we can truly express ourselves without compromising on our privacy. ■