Is it permissible to wear women clothes in total privacy without anyone watching it. Not for sexual purpose but to release pressure?
The Chinuch says in Mitzvah #443 in reference to the prohibition of men wearing women's clothing: "ונוהג איסור זה בכל מקום ובכל זמן-This prohibition applies in all places, and at all times."
So, it seems pretty clear that it's not allowed in any sort of setting.
In general, you should know, that the mitzvot apply equally in public and private. For example, no one would suggest that pig is permitted to be eaten when in private. This can be seen from what are Rabbis stated countless times: That a decree ("גזרה") that was put into force by the Sages is also prohibited "בחדרי חדרים-In the innermost rooms," even though it may seem that the decree was only enacted to ensure that people watching wouldn't become confused. This would apply all the more so for Torah prohibitions.
I read the question with a great sense of concern for the questioner. I was reminded of statements by Rabbi Kalman Topp who reminds us that “the Torah is both a Torat emet — a Torah of truth conveyed through laws and values, as well as a Torat chesed — a Torah filled with compassion. A religious Jew is compelled to grapple with this dialectic and integrate both components,” Topp says also say” we adhere fully to our tradition of Jewish law without denying the commandments inherent in it. At the same time, we recognize that a core element of that tradition is to appreciate — with compassion and respect — the humanity of every single individual and act accordingly.” I offer a summary of some of the thinking around cross-dressing. I wonder if the more lenient view would not be supportive of private-cross dressing as it does not seem to amount to the “violations” that the halacha seems to seek to avoid.
The biblical prohibition against cross-dressing occurs in in Deuteronomy 22:5 A man's attire shall not be on a woman, nor may a man wear a woman's garment because whoever does these [things] is an abomination to the Lord, your God.
The question on cross-dressing arise in the Talmud Bavli Nazir 59a as a point of disagreement between Rabbi Eliezer ben Ya’akov and the Tanna Kamma. Rabbi Eliezer ben Yaakov forbids any situation in which a man dresses like a woman or a woman dresses like a man, whilst the Tanna Kamma objects that the Torah only forbids this in a situation of to’eva (a repugnant act), which would only occur if the purpose was to allow a man to sit among women or a woman to sit among men.
Rashi (c. 1040-1105 C.E.) commenting on Deuteronomy 22:5 and drawing on the Talmud Nazir, 59a says that the prohibition is limited to concealing identity for the purpose of adultery. With respect to a man wearing women’s clothing Rashi says: “Simlat Isha, a man shall not wear a women’s garment: So, he can go and be among the women.” If a man dresses as a woman, he can sneak among women for sin. A married woman walking to a secluded place with a man will fall under suspicion. If she walks with what looks like another woman, no one will ask questions. Likewise, for a woman wearing man’s clothing “Kli gever, a man’s item should not be on a woman: That she should not appear as a man so she can go out among men, for this is only for the purpose of adultery.” Rashi explains the moral force of this: “To
eva, abhorrence: The Torah forbids only garments that may lead to toeva, abhorrence.” Rashi seems to limit the prohibition to this case. Thus, men and women cross-dressing in other circumstances might not be prohibited, at least if it can be assured that the “abhorrence” will not result. Essentially according to Rashi, cross-dressing is forbidden because it facilitates the breaking of miztvot.
However, Rambam explains it differently. The Rambam, Hilchot Avodah Zara 12:10 follows Rabbi Eliezer ben Yaakov’s opinion that wearing women’s clothing of any kind is completely prohibited. In Sefer Ha-Mitzvot, prohibition 40 he states that the prohibition has two reasons. First, cross-dressing was an ancient idolatrous practice; it was part of certain rituals. In order to distance us from idolatry, the Torah prohibits a number of pagan ritualistic practices. Additionally, crossdressing is a form of impropriety, and leads to, sexual impropriety.
Unlike Rashi he says that people sometimes cross-dress in order to arouse their desires, which then leads to improprieties. According to Rambam, cross-dressing leads to arousal which itself leads to the breaking of mitzvot.
I know there are further opinions but perhaps these are helpful.
this forum is probably not the place to get into detailed halakhik dicussions, and I am certainly not qualified to engage in such discussion, but the tur in yoreh deah on the siman about crossdressing cites the gemara in nazir and both tanaic opinions are brought down by the tur and bet yosef. I do not have access to the sefarim right now, but it is easy to locate. one of the tanaim in masekhet nazir clearly says that crossdressing per se is not what the pasuk intended to prohibit because crossdressing itself is not a toavah, and rashi on chumash in ki tezeh brings this lenient opinion to explain the posuk and accordingly the prohibition is only if it is in a situation that can lead to a toevah which is a prohibited sexual intercourse. while the other tanna disagrees and prohibits a broader range of cross gender acts even if apparently there is no intent to commit any prohibited sexual act, in dire circumstances one can rely on a single tanna especially since it is 2 individual tannaim as opposed to a yachid and rabim. I discussed this with a major posek that agreed but only in dire circumstances. I am not, however, saying that anyone should rely on this, rather, look for an intelligent posek who knows about the realities of what crossdressers are really about. the classic poskim on this siman do not discuss the situation of shaat hadkhak - or psychological anxiety which can be significant for a crossdresser.
This entire discussion would only apply if there was a specific clothing that was exclusively for genetic born females. (As was the case in the time of chazal)
Since nowadays transgender is accepted all feminine(and masculine) clothing are intended for both genetic born sex to choose what style they prefer, essentially rending all clothing halachikly unisex.
"דביתהו דרבי יהודה נפקת נקטת עמרא עבדה גלימא דהוטבי כד נפקת לשוקא מיכסיא ביה וכד נפיק רבי יהודה לצלויי הוה מיכסי ומצלי וכד מיכסי ביה" (נדרים מט.ב)
"אמר רב יהודה אמר שמואל ואפילו להבחין בין בגדו לבגדי אשתו אמר רבא לא אמרן אלא דבני מחוזא" [רש"י:מפנקי ולא עבדי מלאכה ובגדיהם רחבים כשל אשה וצריכים עיון] (שבת יב.א)