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Boy, Interrupted

Purim calls for costumes, and we’re fine with seeing little girls dressed up as boys. But a boy dressed as a girl makes us uncomfortable, thanks to stubborn ideas about gender roles. It shouldn’t.

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My favorite Purim costume was Pharaoh. (Don’t fence me in with your narrow isolationist notions of confining oneself to villains of the Persian Empire.) My uncle Michael had given my mom a gorgeous gold-and-turquoise robe with navy embroidery around the neckline; it became my default dress-up outfit. Occasionally, I was Haman, because I enjoyed drawing a twirly mustache on my upper lip with an eyeliner pencil.

While most little girls see the megillah reading as an opportunity to bust out the Disney Princess garb, there are always a handful who get a kick out of being Haman, the way I did. But on Purim this year, which arrives Saturday night, there are likely to be very few, if any, little boys dressed as Esther.

Why? Because when little girls dress “boyishly,” everyone thinks it’s cute. I adored putting baby Josie and baby Maxie in Osh-Kosh engineer overalls and teensy black Converse high tops. If I’d had sons, would I have put them in pink onesies and glittery parachute pants?

Yet many parents do have what Sarah Hoffman, a Jewish writer who blogs pseudonymously, calls “Pink Boys.” (It’s the title of her forthcoming book). Whether a kid is growing up in Berkeleyest Berkeley, Calif., or in Hasidic Williamsburg, Brooklyn, the urge to be fabulous isn’t something entirely within the parents’ control. “Gender identity isn’t something we just impose on kids and expect them to suck it up, like eating vegetables or going to school,” Hoffman writes. “It’s part of who they are, whether that satisfies us as parents or not.” Sometimes, little boys who love dresses grow up to be gay. Sometimes they’re transgender. And sometimes a pretty dress is just a pretty dress. Parents needn’t jump to any assumptions about what a little boy’s love of tulle means, but they should listen to and respect the individual child’s desires.

“Don’t get ahead of yourself,” said Julie Holland, an assistant professor of psychiatry at the NYU School of Medicine. “The important thing is not to induce shame in your kid. It’s essential that kids feel they are OK, that they are loved and lovable.She offered advice to parents whose sons want to wear dresses to school. “You can say, ‘In our culture, many people think that only girls should like pink, and that’s kind of silly. They think some toys and outfits are ‘boyish’ and some are ‘girlish.’ How do you think people will respond if you wear the dress to school?”

The trick is balancing your child’s safety with his or her self-expression. You have to find this balance without letting your own gender-issue mishegas get in the way and without making your kid feel judged and wrong. If your child’s teacher is supportive, the school is a nurturing place, and your son’s passion for silk charmeuse is implacable, why not let the kid wear a freakin’ dress? The issue, of course, is if the school environment isn’t supportive. “You don’t want to hurt him, and you don’t want the world to hurt him,” said Holland. “Which means the ultimate solution is to change the world, not your kid.”

That means if your kid really wants to wear dresses, you find allies within the school community to protect your child. If the kid is experiencing regular bullying, it may mean finding another school or homeschooling. “The path isn’t easy,” Holland added. “But your job as a parent is to, as much as you can, create a safe space for your kid.”

There has conveniently been a boomlet in children’s books about boys in dresses. I can think of four books published in the last year alone that address this issue. 10,000 Dresses, by Marcus Ewert, gorgeously illustrated by Rex Ray, is the story of a child named Bailey who looks like a boy but knows she is a girl inside. She dreams of wearing brilliant dresses made of crystals, rainbows, flowers, and windows, but her family refuses to acknowledge her true self. Ultimately she does find a supportive friend. Unfortunately, I think this book would baffle most little kids: Its use of pronouns is very confusing for kids who view the world in binary ways—the omniscient narrator assumes that the reader understands that Bailey is a she, despite looking like a he, but most kids won’t make that leap. The pictures are gorgeous, though, and I can see older children who are already familiar with transgender issues really loving the book. (Also fun: the blurb by fashion-designing Jew Isaac Mizrahi: “I love this book! If I had read it growing up, I might have felt better about my dress-wearing habit!”)

Then there’s Be Who You Are by Jennifer Carr, illustrated by Ben Rumback, a picture book based on the author’s own parenting experience raising a transgender child. And My Princess Boy by Cheryl Kilodavis, illustrated by Suzanne DeSimone, the story of a little boy named Dyson who likes to wear a tiara sometimes and jeans sometimes. Kids may be turned off by the illustrations, depicting people without faces (each character has a blank oval where the face should be, perhaps so everyone can project herself into the tale, but I think it just looks creepy). The book, by a mom who had a harder time than Carr in coming to terms with her child’s identity, pleads:

If you see a Princess Boy…
Will you laugh at him?
Will you call him a name?
Will you play with him?
Will you like him for who he is?

The one middle-grade novel in the bunch is The Boy in the Dress by David Walliams, a comedian who I am told is super-famous in England. The sweet, stylish spot illustrations are by Quentin Blake. The main character, 12-year-old Dennis, is a soccer-mad boy who loves to read Vogue and gradually admits to himself that he wants to wear dresses. The most popular, most gorgeous girl in school, on whom Dennis has a crush, befriends him and encourages him. There’s a lot of goofy, broad physical comedy (very British) and an ending that was, for me, too unrealistically rosy. But Josie, my 9-year-old, went crazy for the book, reading it over and over. I realized that for Jo, a child with an acute awareness of injustice, the book was a perfect fairy tale. She loved the ending precisely because it would never happen in the real world. What I saw as weakness she saw as wonderful.

Alternatively, as you consider the issue of dressing up—or cross-dressing-up—this Purim, you could always turn to our sages for advice. Deuteronomy may include a prohibition against a man wearing women’s clothes, but Rashi wrote that this kind of dress is wrong only when it leads to adultery, and Maimonides added that cross-dressing is wrong when it is for the purpose of idol worship. To these wise rabbis, the prohibition is against cross-dressing in order to do harm. If harm’s not the goal, as Rabbi Elliot Kukla and Reuben Zellman point out, quoting the Babylonian Talmud: “v’ein kan toevah”—there is no abomination here.

Will the world become more tolerant of boys in dresses? Holland offered a surprising analogy. “Until recently, peanut allergy wasn’t taken seriously,” she said. “Now every school has a policy, and everyone accommodates it. But parents had to educate people about the special needs of their sensitive kids. I’m not comparing cross-dressing to allergies. I’m just saying with education, change is possible.” And maybe that means one day we’ll see a lot more little boy Esthers.

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We have several photos of our son, at 3 or 4, very happily posing in his Esther costume. He wore the costumes to the Purim carnival at our Burlington, Vermont, synagogue, and as far as I can remember received only complements. I look forward to the day when the spirit of tolerance that still characterizes Burlington is more universal.

Thanks for this. I hadn’t heard of these books, and I love how you’ve woven reviews into the medical, rabbinic and personal.
Unlike the universal nature of Ruth’s comment above, my community is a bit more, well, dangerous where gender boundaries are threatened. But, age matters. I notice it’s okay (funny, chutzpadiche, brave) when grown men cross-dress for the Megillah reading, but I have never seen a boy decked out as a girl for Purim. I guess we are more comfortable knowing that these adults are indulging in rabbinically-sanctioned topsy-turviness and that we needn’t suspect any category-confusion undercurrents. It’s kosher.

I had a hard enough time last week at my Purim workshop, protecting toddlers and preschoolers from well-intentioned adult helpers urging them to choose between the Girl crown and the Boy crown. I tried Fancy and Regular, but the grownups didn’t buy it.

Great comments.

Thanks for bringing up the male cross-dressing megillah-readers, Joanna. I couldn’t figure out a fluid way to fit it into the story, but I was thinking about how that kind of dress-up is generally played for laughs, with an element of mockery. As you say, the POINT is that it doesn’t actually challenge gender norms at all, but rather reinforces them.

Jessica says:

My son has a “princess boy” in his pre-K class, who sometimes wears jeans and sometimes wears a tiara. He loves to play princess and he loves Rapunzel. When they play Star Wars, he starts as an evil villain who is killed and then comes back as a princess. His parents are supportive but not pushy one way or another, and the kids are very comfortable with counting him among the girls, as he prefers, but I spent an afternoon in the classroom and was appalled to see a teacher bait this child into identifying as a girl, just so she could scold and say “no, you’re a boy,” looking at me for confirmation which I would not give. If only the adults in the classroom could have the understanding and flexibility of a bunch of 4 and 5 year olds.

Susan says:

The cross-gender Purim costumes have never been a problem in our house. My husband and a buddy used to dress up as Vashti (both of ‘em) for Purim when our boys were little. My older son went as a nurse one year, and Mrs. Lot the next!

Thanks so much for including my writing in your post! I’m so glad to hear you talking about changing out culture, not our kids–but acknowledging that safety comes first. It’s a difficult balance.

I just put up my now-annual Purim post:

Thanks again,
Sarah Hoffman

Abbi says:

I grew up in Modern Orthdox home and my brother dressed up as a girl one year, I think when he was 10. He wore my clothes. I don’t remember it being a problem. I don’t really get hung up on these issues. I’m fine with my son wearing a headband of his sisters’ to gan (at age 2) and I’m fine with him enjoying playing with cars.

Claire says:

My son was a skinny 13 year old when he wore one of my sundresses for Purim. He was…fetching. I was pleased he had the self-confidence to pull it off.

The article isn’t religiously balanced. The rabbis quoted in the article are Trans-gender activists, not universally renowned rabbis; do a Google search. Why not quote orthodox rabbis on the issue. I think it would be better to understand what our religion says on this issue from people who keep the religion seriously, not like us who treat is a last thought when we do something. They still know that the Torah is from g-d. Our religion says for a man not to were women’s cloths to safeguard against adultery. We should keep this custom to prevent it even if it doesn’t seem relevant. Now, lets entertain the ideas of these two rabbis and say that there logic is sound, while it isn’t and you should check for yourselves and see what Rashi says himself. What about giving the impression you are a women! There is a Jewish law that says that misrepresenting the truth (Ganavis Das) Stealing a person understanding is forbidden. How would they answer this question? Now choosing to dress your boys in womens outfits isn’t proper because you are not teaching your child Jewish values, but rather secular values. Just so you know.

Renee says:

My middle brother used to wear the hawaiian mu-mu my grandparents had given me along with my mom’s old 1960’s-era wig and her shoes, and, carrying a pocketbook, walk up and down the street as “Gloria”. He continued this behavior for some time, even influencing our younger brother to do the same (in my brownie uniform). My mom, in 1978 in Texas, voiced her concern to me, age 10, and I remember how hard it was for her not to say anything to the boys. But she didn’t. “Gloria” is now an orthodox Jew with 3 children. You never know, but the important thing is, as a commenter said above, not to shame. Looking back, I am so impressed with my mom’s response (or rather lack thereof). Now I have my own son, and I admit that my husband and I struggled with the issue of how to dress him. Although I am committed to feminist ideals including acceptance of all–wherever we are on the gender continuum–I dress my boy in a conventional boy way. But he has a play kitchen and a babydoll, too. Which he adores. It’s a sticky wicket.

Although I am neither a Jew or a mother to a son, I find this post to be the sanest I have read on this all-of-a-sudden hot topic. The compassion for kids and parents who find themselves outside the “normal” (for good or ill) dress code, coupled with restraint and concern for a child’s safety rather than his (or mom’s, more likely) need to make a public statement, is refreshing as it is, well, motherly: putting the kid’s well-being ahead of all else, even when such action may compromise a political view of the way the world should work.

Sarah, thanks for visiting. Please keep me posted about your book.

I talked to the mom of a pink boy for this story but her quotes were cut for space. She too talked about the challenges of the school bathroom and hallways. You’re right — schools can only do so much. (And right now, they’re not doing enough.) Parents have to take ownership of their “good” kids’ bullying behavior.

My then-nearly-3 year old was planning on being Tinker Bell for Purim last year. When I had mentioned this to an unnamed relative, the following dialogue ensued:

Relative: I pity him.
Me: Why?
Relative: For having to take all the negative comments that people are going to make.
Me: You know what? I pity the adults who are so narrow-minded that they would feel compelled to make negative comments to a toddler about his choice in Purim costumes.
Relative (throwing hand in the air): You’re impossible when you get like this.

This year, he’s planning on being Batman. At least, that is his plan today. He might very well change to one of his princess “uniforms.”

Tovia says:

This comes from a mom who let her daughter dress as Buzz Lightyear, but here’s a thought that occurred to me…Doesn’t Torah, the foundation of the Bible in which Esther is contained, tell us to diligently teach G-d’s mitzvot to our children…one of which is that men should not wear the clothing or anything pertaining to women and women likewise? If we fail to teach this principle to our children, are we transgressing Torah?

JCarpenter says:

The issue to me is one of context and atmosphere—it is a party, not reality; situational comedy/drama/role-playing goes back in the drawer/on the ooathanger when the storytelling is over. Society has established boundaries and roles, which often need to be challenged/stretched/broken, but equally as often need to be observed, time being. Along with “fixing” society, we should also not put an all-or-none status on role-playing when it comes to gender identity. Is the only role for a little girl that of a passive princess, wearing pink and purple? Is the only role for a little boy that of an aggressive muscle-bound super-hero?

JCarpenter says:

To Tovia:
I remarked to a mother whose son was dressed as an angel for their church’s Christmas pageant: “Is this appearance characteristic of him or ironic?” Her reply: “He has a Buzz Lightyear costume at home, so he’s used to wearing wings.”

Ellen says:

A trend in recent years in certain NYC high schools is for the boys to dress up as girls on “gender bender” days and on the senior trip. They are hilarious, with the wigs and makeup and all. Hmmm!

My son wants to be Batman and Queen Esther. What do you think that means?

I wonder if any of the over-eager halakhic advice-givers here know just how qualified the prohibition on cross-dressing is. For starters, cross-dressing on Purim is strongly RECOMMENDED by the Rema. Food for thought.

In the Shulchan Aruch Yoreh Deah Siman quf-peh-bet for additional heter, like for example if the clothing is functioning to keep the person warm or out of the sun. See also Magen Avraham Orech Chayyim shin alef, siman qatan nun dalet.

In general there’s a principle that once someone has found a way to permit something, even should it be something outlandish such as “making the sheretz tahor,” we should be careful not to be more strict than the minimum the law requires. It’s both halakhic and compassionate to approach people you see in differently gendered clothes as if they have a good reason to do so, and keep your suspicions or disapproval to yourself.

Loved the description of the Rambam as a trans activist, though.

Joel says:


Then explain why no one in an orthodox community cross-dresses on Purim. Not Chassidum, not Yeshivish, and not the Sefaridim. I haven’t seen it in America or Israel. Now seeing Ashki’s follow the Rema why don’t we follow this as the preferred way to do the mitzvah then; because you used the word “RECOMMENDED”?

Thanks for this very thoughtful and helpful piece.


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Boy, Interrupted

Purim calls for costumes, and we’re fine with seeing little girls dressed up as boys. But a boy dressed as a girl makes us uncomfortable, thanks to stubborn ideas about gender roles. It shouldn’t.

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