My son the cross-dresser

September 27 | Guest post by Sarah Tuttle-Singer
Photo by author.
My son is big into tractors. He loves Lego. He builds skyscrapers out of wooden blocks, and then goes all Godzilla on them. He plays in the mud, and looks for bugs, and has a thing for dinosaurs. And on the first day of gan (preschool) last week, my son told me he wanted to wear a dress.

"This dress," he said, reaching for the pink frock with the purple butterflies on it that I had ordered online over the summer. "This dress is great for twirling," he added, touching the ruffles around the edges.

He was right. It was the dress perfect for twirling. And that's exactly what he wore.

"Do you know your son is wearing a dress?" one father asked me during drop-off.

(No! Really? Must be laundry day, Captain Obvious, because you forgot your cape.)

"Maybe he wants to wear this instead?" a mother said, handing me a shirt from her son's bag.

(Right, because nothing screams "manly" like a shirt with a yellow duckling on it.)

"Doesn't he have boy clothes?" a grandmother asked when she saw my son twirling around in his flowery frock.

(No, lady, I've decided to exercise my God-given right as his mother to turn him gay, so it's dresses or nada. Now, lets crank up the Madonna and get this party started!)

O.M. Hashem, people. Get a grip!

Yeah, my son is wearing a pink dress with ruffles and butterflies. But so fucking what? It doesn't impede his ability to play in the dirt. He's not tripping over the hem and hurting himself. Yeah, he's twirling a little bit, but it's awesome: he's learning about rhythm and movement, and about the way soft fabric feels against his legs when he whirls around in a circle.

I didn't encourage his fashion pick: believe you me, our drawers are stocked with clothes in navy blue, steel, and hunter green. We have shirts with pictures of dinosaurs and trucks and cartoon dogs emblazoned on the front. He has the requisite badass AB/CD (AC/DC parody) T, and when he was a baby, he rocked the "Chicks dig my Crib" onesie. But when my son gravitated toward his sister's skirts and dresses over all the clothes in his drawer, I honored his choice.

Yeah, my son is only two-and-a-half years old, but this is one way I can let him (safely) exercise his autonomy. Sure, there are things that parents decide for their kids all the time: If asked, my son might have opted out of his brit, or the DTaP vaccine. But this is different.

And if anybody — parent, or teacher, or child — belittles my son for this, I swear I will fillet them. Because even if he starts breastfeeding dolls or asking to take ballet class, so long as he's happy and healthy, then it's all good. And I will honor his choice to wear dresses, or lip-sync to Like A Prayer or wear red nail polish on his toes.

Or fall in love with whomever he chooses.

(Although Little Dude better get his own high heels.)

We live in Israel, and in a country that places such a high premium on machismo it won't be easy for my son. But in the meanwhile, he's learning how to own his choices. When the older kids say "Why are you wearing a dress?" he says: "Because I want to."

And when one of the savtas on the kibbutz had the nerve to speak to my son in female verb tense — knowing full well that he's a boy — he said to her: "Stop it. I am not a girl. I'm a boy. And boys can wear dresses."

And, guess what? Turns out my son is a trendsetter. A few days ago, another little boy showed up to gan in a purple tutu.

  1. This just makes me happy, like so freakin happy!! Thank you 🙂 You're teaching your son how to be confident and happy with what he loves and who he is. This is exactly how I want to raise my daughter, and I hope we are on the same path you are.

    It took me years to have that kind of confidence in who I was and what I loved, to see it in someone so young fills me with such hope and such pride in a little boy I have never met.

    1 agrees
  2. I love this whole article. I love that you have respect for your son as a whole person and you find the ways he can safely exercise his voice and support him in those. I'm sure he will thank you, one day, and many days, as he grows into whoever he will be.

    5 agree
  3. When my 8 year old daughter was small, she loved Thomas the Train and Diego (from Go Diego Go). She wanted Thomas t shirts and underwear with both those characters on them. As those are only made for boys, guess what? She had boy undies. At these ages, so many things are fluid and undecided it has absolutely no bearing on what he will do when older. It may, it may not. However, my 8 year old is now a thoroughly girly girl. She still thinks dinosaurs are relatively cool (after loving them for years. An eternity in kid world). But now, it's all about the pink, and princesses, and dolls. Other parents need to get over it at this age really. 🙂

    7 agree
    • Yeah, when you're a kid, you want lots of different things. It means nothing. People know what they're taught. I wanted to put on nail polish when I was about 4, but my Mom kiboshed that, so I did it with markers instead. I wanted to wear her dresses too, but she wouldn't let me, so I snuck into her closet and did it anyway. I'm 35 now and have never worn women's clothing or put on nail polish since then, nor have I wanted to.

      1 agrees
  4. You see the bigger life picture that so many people miss and I appreciate that. I have a son and feel the same way about this issue. 20 years from now your son won't remember the time when his mom wouldn't let him wear a dress to school. He will remember the time when his mom loved him unconditionally, regardless of what he was wearing and that, to me, is far far more important.

    1 agrees
  5. So often parents will do anything for their children–except let them be themselves.

    You are doing everything you can for him.

    24 agree
  6. My sister's favorite color is and always has been blue. Try finding little girl's stuff in blue in the mid-eighties. It was impossible. So she often opted for the "boy version" of toys. Her first Big-kid bike was a boy's bike because it was blue. I was happy my parents honored her choices then and I'll definitely do the same with my little one. By the way, my sister still loves blue and grew up to be a heterosexual and even feminine woman…not that there would be anything wrong with her ending up any other way! Bottom line is that people need to stop freaking out and just let kids be happy while they are still young and innocent.

    2 agree
  7. I used to teach at a small alternative school in Texas, and one of the 5-year-old boys in my class used to wear his sister's old dresses. I loved it. He said he only wore the ones that spun the best. A few people raised eyebrows, but if anyone asked him why he wore dresses, he'd simply say, "because I want to," and that was it. He's 14 now, and I've heard from a mutual friend that he's a super cool kid who, to our knowledge, doesn't wear dresses anymore. I think knowing that they are trusted to make their own decisions about things like that when they're little instills a unique confidence in them as they grow. Good for you, mama!

    1 agrees
  8. This is awesome. I can only imagine how hard it would be if you thought about what everyone else would think of your son, especially in the area you live in. Instead you think of how your son would feel, and go with that instinct. I'm not a momma yet, but reading articles like these helps my mind face these subjects with openness – subjects I don't think I have the imagination to conjure up in my spare time.

  9. I live in an extremely liberal, hippie town. At our town fair, I was walking with my four-year-old and we passed a booth filled with tie-dyed clothes. He grabbed my hand and looked at me anxiously and said "do you think they have boy dresses in there?" Absolutely! But even the hippy lady in the booth took a few times to get the fact that we were looking for a dress for THIS KID HERE, THE BOY RIGHT IN FRONT OF YOU. I got one dress for my 4yo and one for my 2yo son. My 4yo insisted on wearing it right away, and as we walked through this festival of drunk, stoned people twirly dancing and partying, we still got tons of double-takes. We approached one group of early-20s boys who started commenting so I looked the ringleader right in the eye, grinned and said "Yeah? It's a boy dress!" He stopped for a beat and decided to be cool — gave my son a "right on, bro!"

    1 agrees
  10. My 4.5 year old boy has been frequently wearing dresses and those little pink plastic high heels for some time. Often people refer to him as a she but he doesn't really seem to notice or care.
    I totally agree with everything you say, who the heck decided only girls could wear frocks anyway? To be honest we haven't had much resistance from people except his grandad not wanting to take him to church in his favourite pink ballerina cardigan.
    I'm not really into the whole gender rules thing – boys must do A and Girls must do B, and have always had a few girly dress ups etc. He mostly chooses superheroes but sometimes superman has a purple boa, pink beads and some little high heels. Looks cute!

    4 agree
  11. I'm happy to let you know that a little boy wearing a dress is nothing new. 18th, 19th, and early 20th century mamas dressed their sons in dresses until they reached about 6 years old when they were "breeched" (put in "grown-up boy" clothes for the first time).

    Here are some pictures to prove it:

    http://1.bp.blogspot.com/_7XLvQTao2k8/TTTIJSzgYOI/AAAAAAAAHBI/74HpGMWPQio/s1600/har+and+co.jpg

    http://www.colonialsense.com/Antiques/AuctionResults/12-01/stock.jpg

    http://www.yourememberthat.com/files/e9aee4a97d857d9b.jpg

    The first picture is of Henrietta Ponsonby, Countess of Bessborough (sister of Georgiana Spencer, Duchess of Devonshire) and her little men. The second picture is a painting entitled "Portrait of a Boy" and is attributed to 19th century painter Joseph Whiting Stock. The last picture is President FDR when he was little.

    My point that if little boys from bygone eras could wear dresses, why can't modern day boys?

    1 agrees
      • You make a very good point there. I'm of the belief that boys and girls can wear any color they please. The pink and blue thing just reinforces gender roles and stereotypes.

  12. Your kid is awesome! I have a two year old myself and no lie, he can walk in my heels better than I can!

    The "Nothing screams manly like a shirt with a duck" bit made me snort. 🙂

    1 agrees
  13. I'm always ultra interested every time I read something like this that reminds me of the power we give to clothing.
    Clothes are pieces of fabric stitched together so that they cover the body. They are not physically part of us and they have no significance other than that which we assign them.

    But, whoa, do we ever assign them significance.

    I'm not a child psychologist so those who have that background are welcome to correct me, but it seems highly unlikely to me that a 2.5 year old would have already internalized the cultural gender significance of "the dress" enough that the child is making a cultural/political statement with their clothing choices.

    I really doubt that, at that age, a boy wearing a dress is doing it specifically because he identifies with being a girl or is romantically attracted to boys. This seems to be the implications of the comments the article writer received. It strikes me as far more likely that it's because he likes the colour or because someone else who is interesting to him wears dresses (like an older sibling he admires)…or because, as the writer's son declares, the twirling thing is cool.

    As a lover of twirly dresses, I concur. Twirling is cool. In fact I think lots of girls who wear dresses do so because twirling is cool.

    There's also a double standard here since I bet there were plenty of pants wearing little girls at school that day and no one gave their parents a hard time for their clothing choices. No one assumed that a two year old girl at the school in pants was outing herself as a lesbian. Why make that assumption about a boy in an awesome twirly skirt?

    Yes, statistically speaking, a certain number of young boys will recognize that they are gay at some point in their growing up process – and I suppose that those boys who are allowed to explore options in life are more likely to come out to those around them because they will feel safer knowing they are allowed to be who they are. So I suppose it's possible that some boys who wear dresses when they are young will wind up identifying as gay and perhaps people will remember the dress wearing stint.

    Of course, some young boys who appear to fit all traditional gender characteristics also grow up to identify as gay so the wearing of a dress is not a major factor.

    As for the idea that a boy wearing a dress is more likely to be bullied, well it's possible, but I don't think forcing one's child's clothing choices is the solution. Kids get bullied for all sorts of things and our response generally isn't to tell the victim to change. We don't tell kids who are bullied for doing well in school to start failing so that the others won't make fun of them. A

    Sure, if he keeps wearing dresses, someday someone will declare to him "that's a girl's outfit" in a tone of voice that makes it clear the speaker disapproves. And then the writer's son will have a choice to make, but most kids face that with something:
    "You have a Dora Shirt, Dora is stoopid."
    "You can't like math, it's not cool"
    etc.

    And frankly, the dress wearing boys in the article and comments seem to have more than enough confidence to respond to those comments with something resembling "So what? I like it."

    1 agrees
  14. LOVE THIS. When our son starts preschool, I hope he has as strong a sense of himself as yours does! Speaking as someone who made some socially unaccepted choices as a very small child (clothing, media consumption, and more), I bore my "stigma" as a badge of pride in later years. I feel like it validated my choice to not conform to trends or social conventions that didn't fit who I was: I had set the precedent of making my own decisions, and eventually the pressure disappeared altogether!

    1 agrees
  15. Your son is just a whole lot of awesome! I love that he is such a fantastic individual and is not afraid to tell people so.

    2 agree
  16. I'm amazed that people still get riled up about these things (well, not amazed, since I grew up in a very conservative area, and remember how bent out of shape people get about this stuff).

    All kids have always loved dressing in all kinds of clothes that are fun and fluffy. BECAUSE THEY ARE FUN AND FLUFFY.

    Like others, I'm delighted that you are letting your kid be who he is.

    1 agrees
  17. I love how your son responds to questions and statements from others, and that you're right behind him. Rock on!

    2 agree
  18. You are awesome! I loved your little side comments too (captain obvious and the Madonna thing). <3

    The way I see it, boys and men wear kilts… so whats so bad about wearing a normal skirt?

    2 agree
  19. It seems possible to me (Not having been there to here the tone, etc.) that the person who spoke to your son in feminine verb tense might have thought (incorrectly but not entirely unreasonably) that he wanted to addressed as female when he was wearing the skirt, either because of his basic gender identity or because he was he was pretending to be a girl in some kind of dress-up game, and have been trying to accommodate that. Either way, he set her set her straight very clearly. So good job, kiddo.

    1 agrees
  20. This was a very well written article, and, like the others, I applaud your ferocious support of your son's personal choices and individuality.

    However, I am shallow. So I must confess that my favorite thing about the article was not your motherly badassery or your son's beautiful self-confidence, but rather this line:

    "(Although Little Dude better get his own high heels.)"

    Because you're so hilariously right on. 🙂 My stilettos are sacrosanct! 🙂

    1 agrees
  21. Why do clothes have to have such distinct gender bias?! They're just clothes! Your son is awesome for wearing what he wants.

  22. I loved this article and all the comments! I remember on a 'school spirit day' in elementary school everyone was supposed to wear pink and the class with most participants got prizes. One boy in my class wore his sister's pink dress because it was the only pink clothing they had in their house. And he got sent home from school 🙁 I don't remember kids making fun of him, just the principal saying that it was 'not allowed'. This was early 90s. So glad things are changing for a new generation!

    1 agrees
  23. Love this! When I was a little kid, I hated it when my mom made me wear dresses. I always felt naked in girl's clothes. Now I my husband and I share most of our wardrobe. There's nothing wrong with being comfortable in what you wear.

  24. Awesome!! I posted a couple of pics of my 4.5 year old wearing dresses I had put away for his little sister to grow into, on Facebook last night & a lovely friend linked me this!
    My sons Dad hates when I paint the little mans nails or let him wear lipstick… so the dresses didn't go down very well but I just keep telling him, denying the little guy a chance to have fun NOW, will only make it MORE attractive when he's older!
    And even if it remains attractive, so what! Thanks for sharing this! Wonderful!! x

  25. Awesome!! I posted a couple of pics of my 4.5 year old wearing dresses I had put away for his little sister to grow into, on Facebook last night & a lovely friend linked me this!
    My sons Dad hates when I paint the little mans nails or let him wear lipstick… so the dresses didn't go down very well but I just keep telling him, denying the little guy a chance to have fun NOW, will only make it MORE attractive when he's older!
    And even if it remains attractive, so what!

    1 agrees
  26. F'in fabulous. I especially like that he is learning to own his choices and protect his self-esteem. Bravo!

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