Question: If a chosson or bar mitzvah boy has acne or other facial blemishes that bothers him, and he feels uncomfortable or embarrassed at the family pictures, is it okay for him to use a cream or makeup that is generally designated for women to cover it over, or is doing so prohibited under the prohibition of lo yilbash?
Answer: In regard to this shailah, R’ Yaakov Skoczylas shlita writes as follows: It would appear to me, in my humble opinion, that in such a case it is permitted for a man to use a cream or makeup in order to conceal blemishes, and there are several grounds for leniency, which we will briefly outline, b’ezras Hashem.
The Gemara in Shabbos (50b) cites a dispute as to whether it is permitted to remove scabs from a wound on the body, lest this involve a violation of lo yilbash, since it may appear as though one is imitating women. The halachah follows the opinion that permits it, and there is no concern of lo yilbash. Nevertheless, one might question our case, since here he is using makeup designated for women, which is certainly considered a womanly practice, as we find in several places in Shas. If so, how can it be permitted to use such makeup to conceal blemishes for pictures?
However, Tosfos there already explains that even according to the opinion that prohibits removing scabs, this is only when one does so in order to resemble women. However, when one’s intention is merely to spare himself embarrassment, there is no prohibition of lo yilbash at all. According to this, it would seem that in our case as well, one may permit the concealment of blemishes even through the use of women’s makeup, since his sole intent is to avoid embarrassment and not to resemble women. This ruling is found as well in Teshuos Levushai Mordechai, Mahadura Tinyana (100), who permits such a case, and he further cites proof from the Gemara in Shabbos and from the Meiri, who writes that anything done for the honor of Hashem does not fall under the prohibition of lo yilbash.
An additional basis for leniency is that these blemishes are considered a mum [a defect], and it is permitted to remove them as a form of medical treatment. I have cited elsewhere the opinion of Rav Shlomah Zalman Auerbach, zt”l, who permits this when the intent is merely to remove a defect. Similarly, the sefer Kerem Shlomah (s.k. 25:3), based on the rulings of leading poskim, rules leniently even regarding other blemishes that are removed because they are unsightly. This is also the view of the Rivevos Ephraim, zt”l, that a man who has facial blemishes and is embarrassed by them may remove them, and this does not constitute a violation of lo yilbash.
In Teshuvos Bigdei Chamudos, Vol. 2 (Kovetz Halachos), the ruling of Rav Shmuel Kamenetsky, shlita, is cited: if a young man has acne on his face and a physician wishes to remove it through cosmetic treatment that is generally designated for women, it is permitted to do so and does not constitute lo yilbash.
In practice: A bochur or a man who has facial blemishes and is attending a simchah where pictures will be taken, and is embarrassed by them, may apply women’s makeup to conceal the blemishes. This is entirely permitted and does not involve any prohibition of lo yilbash, since his intention is solely to avoid embarrassment and not to resemble women.