Cross-Dressing My Tot: Does That Make Me a Bad Mother?


christopher robin winnie the poohBefore you call Child Protective Services, hear me out. Sometimes I look at my gorgeous little boy and wonder, "I wonder what he would look like as a she?"

And so I pulled his luscious curly blond locks back into ... my headband.

He liked it.

At the time, I had only a flower print hair accessory. Otherwise I would have chosen something much more masculine like "royal boy" blue or "fire engine" red -- even black, although I'm not a fan of dressing toddlers in that particular color. The same goes for camouflage. I mean, he's still in diapers, not preparing for combat.

Other gender-bending activities include dabbing a bit of lipstick on him, but only because he was watching me apply my own lipstick so intently. And I wanted to play a trick on daddy. You know, make him think mommy was crazy. Funny, ha ha! Right?

Well, maybe that was a bit wrong.

Trust me, these are minor infringements in comparison to what I caught my sister doing: attempting to blow out his curls! She assured me that her setting was on low heat, but that was only part of the problem. Clearly, he's too young for a blowout.

And while I always find those adorable frocks at Target darling, I never cross the gender divide, even though I think it would be a hilarious prank to pull on granddad, showing up in our best Sunday dresses. Ordinarily I live in Spain where boys are routinely dressed in tights during the cooler months. Most of my family in America, especially my father, finds the whole concept entirely -- you know -- girly. I, of course, love the style. He looks just like Christopher Robin in his stockings.

By no means do I wish for my son to be gay like some liberated moms out there, though I have always gotten along famously with gay men. I can honestly say, though, that the sexual activities and preferences of my son way down the line do not interest me in the slightest. Besides, we're talking strictly dressing boys and girls according to gender rules, not identity, as in ladylike pink for girls and battlefield green for boys.

Of course, according to historians, the gender specific color chart is a most Victorian-era concept and those people were quite oppressive, weren't they, working little Oliver Twist to the bone? Those gender-dressing rules are also restricted to country and culture. Take for instance Spain, where frilly lace is standard baby boy attire.  

This being 2010 America, I know that he is not supposed to wear barrettes and nail polish, yet when he looks at me with those curious eyes, I can't help but let him take some of my beauty accouterments out for a spin. He defaults to sticks and cars anyway ... who's to say a little gender subterfuge isn't healthy?

Image via peacay/Flickr

boys, grooming


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KatieP. KatieP.

my son always wants to wear my lip gloss. lol. I have let him. I go the other way tho. my son was first and when my daughter came along I refused to go out and buy pink stuff when I had perfectly good blue stuff. So all of her blankets/sheets/toys/car seat/moby wrap- every thing except the clothes she wears is blue - every one always thinks she is a boy.

nonmember avatar Cassandra

My 8mo old LOVES my brush brush, so he frequently gets blushing powder dusted across his cheeks, forehead and chin. *g*

Bill Jones

"By no means do I wish for my son to be gay like some liberated moms out there, though I have always gotten along famously with gay men."

Total BARF.

Brook... BrookyHBK_Y2J

Hey, look at Shiloh can't tell if she's a girl or a boy anymore. Brad and Angie have her hair short, and she wears all sorts of boy clothes.

I was always tomboyish growing up, never got into anything girly until I was 18. I wouldn't mind one bit if my girls decided to ditch the flowery dresses, makeup, and purses for jeans, a tshirt and a football. It'd make me proud, but no matter what my girls do, or dress like, I still love them.


Lynette Lynette

u're son needs some of those babylegs.  they mak the in boy patterns!

sstepph sstepph

Eh, I pulled my sons hair up in to a pony once just to see what hed look like, haha.

ethan... ethans_momma06

We did the long hair that was clipped or pulled back for quite a while. Not TO genderspecific since you do see a few guy wandering around now and then with pony tails (and generally those guys are def. NOT gay). Attire is what you make it. A little pink, a little frilly lace, etc. isn't 'harmful' unless you go on and on and on about how it's a GIRL thing and he looks so cute dressed like a GIRL.

jus1jess jus1jess

Having long hair isn't a biological indicator of a girl and wearing truck decorated t shirts isn't a biological indicator of a boy. So I don't think any of this stuff matters. My daughter wears "boy" underwear. That doesn't mean I'm trying to make her a boy. If I had a boy, I wouldn't mind him wearing a tutu. That wouldn't mean I was trying to make him a girl. This is all appearance stuff and appearance doesn't determine sex/gender. We've created social norms for which gender wears what and some people have made them rules. It doesn't make any of it right or wrong though. We're all born naked. Everything else should just be style preference. 

Cynthje Cynthje

My son loves my make up brushes, lip gloss and high heels and i let him have fun with it, my daughter loves to play with cars and trucks and i let her doesn't mean anything its just kids having fun. 

Carey... Carey2006

As long as daddy doesn't see....LOL

I don't mind, I just consider it a special Halloween is every day day.


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