A . Let us start by distinguishing between a man and a woman when it comes to dress and fashion, a tznius woman is not only permitted to dress beautifully but she is encouraged to do so for reasons beyond the scope of this particular question.
A man, on the other hand, is not supposed to be overly occupied with his appearance. Preoccupation with fashionable clothing may, in certain cases, even fall into the halachic issue of “Lo Yilbash.” (Similar to the issue brought by the Shulchan Aruch with regard to men using mirrors — see ‘Ask the Rav’ in this weeks issue. Ed.)
This is not to say that looking representable and put together is wrong. To the contrary — seder v’nikayon (order and cleanliness) are of utmost importance and are a show of respect for the body that Hashem gave us.
But like the Rebbe said, “in di zachen darf men nit kochen” — you shouldn’t be obsessed with it.
What is the function of clothing?
The Gemara (Shabbos 113b) quotes Rabbi Yochanan’s statement that “My clothes are my honor.” A person dresses in order to express out his own dignity. Many a time, a person’s self-worth will be expressed in how he dresses. If he has healthy self-esteem and he sees value in himself, that will be expressed in a neat and organized manner of dress. But our occupation with our clothes must stop there.
Clothing should represent us, but shouldn’t define us. If clothing becomes so important to us that dressing simply makes us feel unhappy, that would be bringing out a shallow and superficial side of us that we must work on eliminating.
Clothing is supposed to reflect who we are and what we represent, it should add to our true self, it should reveal and enhance our inner beauty. The more we emphasize the beauty of the clothing, the less we appreciate the inner beauty of ourselves. The more we idolize the external, the less we value what’s truly important, our p’nimyus.
Even a person empty of true inner value, can dress in fashionable clothes, put on makeup and appear to be beautiful from the outside, but there is nothing on the inside to be proud of. That is what the Torah calls “sheker hachein” (false beauty).
The Torah is not saying that beauty is false, it is saying that external beauty alone is false! Let me reiterate: Clothing should represent us, but shouldn’t define us. ■
Lightly edited from a video answer on StumpTheRabbi.org