Is it assur to wear makeup as a Jewish man?

Question

This might fall under lo yilbash, but at the same time the word “simlat” could exclude things like makeup and earrings. I quite honestly don’t know.

Answer 1

If you look at Yoreh Deah 182, it mentions that a woman may not wear male clothing (and vice versa). The last halacha there mentions a man dying his white hair black, which is forbidden.

אָסוּר {לְאִישׁ} לְלַקֵּט אֲפִלּוּ שֵׂעָר אֶחָד לָבָן מִתּוֹךְ הַשְּׁחֹרוֹת, מִשּׁוּם לֹא יִלְבַּשׁ גֶּבֶר (דברים כב, ה) וְכֵן אָסוּר לְאִישׁ לִצְבֹּעַ {שְׂעָרוֹת לְבָנוֹת שֶׁיִּהְיוּ (בֵּית יוֹסֵף)} שְׁחֹרוֹת, אֲפִלּוּ שַׂעֲרָה אַחַת. וְכֵן אָסוּר לְאִישׁ לְהִסְתַּכֵּל בְּמַרְאָה. {וְעַיֵּן לְעֵיל סִימָן קנ״ו.}

I do not see the difference between dying and makeup especially since I don't think men normally wear makeup. If there is a specific makeup for men that would be something you should ask a Rabbi or if you need to wear makeup for work etc...

Note: Shevet Halevi 3:2 seems to not allow dying hair even if men in general do so... Though there is a disagreement on this point, it appears he holds that dying hair is inherently feminine and general custom can't change this. The question would be if makeup is inherently a feminine action (if so custom could not override that), or if it is just customary for women to wear makeup. This would require Daas Torah not a survey.

Also the Halacha in 182 seems to allow a man dying his black hair white according to a number of Poskim there (Taz etc...). I presume it is because a woman does not beautify herself like that and in fact is the opposite result.

שערות לבנות שיהיו שחורות – שזהו נוי אשה אבל איפכא שהיו שחורות וצבע אותם לבנות שרי אפילו לכתחלה כ״כ ב״י

Perhaps makeup that is meant to disfigure (for use in special effects) could allow for a leniency, but a Rabbi must be consulted especially since certain phases might unintentionally beautify etc...

Answer 2

H. A.Z. 12:11[10]:

לא תעדה אישה עדי האיש, כגון שתשים בראשה מצנפת או כובע, או שתלבוש שריון וכיוצא בו, או שתגלח ראשה כאיש; ולא יעדה איש עדי אישה, כגון שילבוש בגדי צבעונין וחלי זהב--במקום שאין לובשין אותן הכלים ואין משימים אותו החלי, אלא הנשים: הכול, כמנהג המדינה.

A woman should not adorn herself as a man does - e.g., she may not place a turban or a hat on her head or wear armor or the like. She may not cut [the hair of] her head as men do. A man should not adorn himself as a woman does - e.g., he should not wear colored garments or golden bracelets in a place where such garments and such bracelets are worn only by women. Everything follows local custom.

There is an element of subjectivity baked into the law on this issue. Whether such actions are permitted depends on whether doing so is normative within the local culture.