Perhaps the real question is not whether a person can or should undress, but rather, what is the best mask to wear.
Is one mask superior to another?
What is the best way in which to dress my identity so it will seem more elevated?
The human being and the dress, the nature and the artifact, the human hand and the tool are all intricately interconnected.
Our unique nature, then, is in our capacity to choose our mask: the demon or the angel.
–Rabbi Adin Steinsaltz
From “Masks” in Simple Words by Rabbi Adin Steinsaltz