Cross-dressing

Discussing the option of an Orthodox man who likes wearing women's underwear to seek a heter

This is probably an odd topic to have caught my interest, but, hey, I’m eclectic. I’ve been puzzled about the commandment regarding men not donning female clothes and women not donning male clothes for a few years now. We currently live in a culture where many clothes are gender neutral. For the last few decades, it has become socially acceptable for women to wear most men’s clothes (e.g. google “women’s pant suits”), and it is currently becoming more socially acceptable for men to wear women’s clothes.

It’s an interesting halachic question as to what is the halachic point where a previously only-for-one-gender garment becomes socially acceptable enough for Orthodox Jews to participate. Think nail polish, earrings, lace, jewelry, headbands, high heels. And of course my personal favorite, Yosef in Mitzrayim and his eyeliner.¹

It’s an interesting “taam hamitzvos” [reasoning behind the commandment] question why Jews are commanded to not crossover. This question, assuming that the commandments are wise and insightful, becomes markedly salient in our culture. Currently we as a society are constantly questioning rigid gender lines and gender roles and exploring how confining and problematic they are for so many of us. Be that as it may, as an Orthodox person committed to halacha, I continue to keep the law even as I question it.

But recently I began reading about cross-dressing. I am NOT discussing transgender, i.e. when you feel like your body is the wrong gender. I think halachic exploration of cross-dressing during gender dysphoria is an important but separate discussion. Transvestism is wearing the clothing of the opposite gender.

transvestism remains poorly understood in America. Considerable confusion exists as to the sexual orientation of TVs…in fact, most Western transvestites are heterosexual.²

many male-to-female cross-dressers deny that they experience erotic stimulation from wearing women’s garb.³

The TV is also apt to have periods, sometimes extended, when he can live comfortably, successfully, and uniquely in his male persona…the majority of TVs lead prosperous, conventional lives as husbands, fathers, and community leaders.⁴

Those who cannot accept their cross-dressing inclination (or who have censorious partners) may go through phases during which they destroy their alternate wardrobes.⁵

I deduce that this destruction is frequently connected to shame.

The urge to cross-dress may become compulsive,⁶ particularly when the TV cannot find meaningful outlets, such as support groups, or compassionate partners. He usually finds that the need to cross-dress escalates when it is repressed. Compulsive cross-dressing can threaten the security of marriages⁷

This is where I began to think it’s important to write an article about this. Once we are getting into the realm of compulsions, this is no longer strictly a halachic issue (Hey, you like to wear women’s underwear, but it’s assur, so control yourself. I’d like bacon but I don’t eat it). This is a mental health issue. I’d venture that this is not discussed very much and that poskim are not aware of this. This could lead to “you should just control yourself” advice, which is terrible advice here, and could even increase shame, increase the urges, and boom—negative shame spiral.

Transvestism is primarily found in males. Clinically, a transvestite is a man who likes to wear clothing socially reserved for women. It has been estimated that 0.1 percent to 1 percent of the male population has this behavior to some degree.⁸

This is where I became determined to write an article about this. If there are about 14 million Jews, about 7 million males. That means that between seven thousand and 70,000 Jewish men might be trying to keep halacha, fighting this compulsion, and feeling bad about themselves and thinking they ought to “just be able to control it.” ⁹ Bear in mind that the compulsions increase under stress, increase when there is lack of understanding, increase when their partner is disapproving. I would say I don’t know any Orthodox Jewish men who like to wear women’s underwear,¹⁰ but more likely I don’t know anyone who has the nerve to discuss it with me.

the desire to cross-dress has [not] been eliminated by any clinical approach¹¹

At this point I have to ask, if a person has compulsions, feels shame about something they can’t control, and it’s a pretty easy fix to just wear the underwear (and be encouraged to share this with an understanding spouse), and medication won’t fix it, and “control yourself” won’t fix it and the urges get worse with stress, it would seem to me that the medical community would suggest that the best thing for mental health would be to do it. Even if medication could help with the urges, which it can’t, should a man go on medication (which has side effects) to stop shame, guilt, or stress that could be alleviated by a heter?

This may seem like a niche soapbox to stand on, but if there are only a few Orthodox Jewish men struggling with this out there and they read this, and it equips or motivates them get the advice of a therapist and be able to speak to a Rabbi and make it understood that this is a strong place for a mental health heter, it’s worth it.

1. The guideline I use is “If you work at a conservative bank, can you wear it to work.” Pant suits, yes. Nailpolish? A tasteful ear stud?
If it’s socially acceptable in mainstream America, but not socially acceptable in yeshiva, is it beged isha? Does it depend on where you are? I wonder these things.

2. Different Loving by Gloria Brame, pg. 418.

3. ibid pg. 420

4. ibid

5. ibid pg. 421

6. my emphasis

7. ibid

8. ibid pg. 430

9. If there are 2 million Orthodox Jews, then between 1000 and 10,000 men are suffering about this.

10. I wonder what the halacha is now that there is definitely lacy feminine underwear made for men. From WALMART. Is this still beged isha?

11. ibid pg. 431