Lipstick & Heels On a Little Boy

Posted On: 09.01.10


Last weekend, we had some friends over to our new place. My friend asked me a simple question, “What do you think about little boys having little strollers?” I told her I thought it was fine. “Me too,” she said. “As long as the stroller is blue.”

It was a simple, unremarkable exchange. But it reminded me of a question I have been pondering off and on for a while now, namely whether we parents should try to “encourage” our children toward “gender appropriate” objects and behaviors. Please note that I use scare quotes here very purposefully as I am not sure where encouraging ends and pressuring begins and I am not sure whether I believe that there are such things as gender appropriate objects and behaviors.

I remember the moment well. Toddler, two at the time, had just made the foray into potty-training. To celebrate this progress, we went shopping for big girl undies. At the store, we stood there, mother and daughter, in front of the display of baby briefs. Another mother and her daughter stood next to us, also perusing the merchandise. As fate would have it, both of our little girls zeroed in on the Diego underwear. Yes, in the boys’ section. This other mother was horrified. “You cannot have those!” She yanked some princess panties from the rack and whisked her girl away. Toddler’s interest in the Diego underwear didn’t wane. Very politely, very articulately, she told me those were the ones she wanted.

I didn’t give it much thought. I bought her two pairs.

To this day, my little girl wears these undies under her little purple outfits. She loves them.

So what? I am not sure, but I have always believed that we should let young kids be who they are. My little girls play with dolls and strollers and trucks and trains. Some nights, they sleep in blue pajamas covered in cowboy hats. Some nights, they sleep in pink pajamas covered in twirling ballerinas.

I let them choose.

Thanks to Lisa Belkin of the NYT’s Motherlode, I became aware of a recent controversy surrounding this ad wherein a little boy is depicted wearing his mother’s high heels and trying her lipstick. In the corner of said images are advertisements for a karate school. The message, presumably, problematically, is Let us toughen your boy up. Apparently this ad, arguably prime evidence of stereotyping and gender-shaming, was published online without the karate company’s consent. Click here if you are interested in the details.

I have a good friend with a little boy. He is a wonderful little boy – exceedingly intelligent and kind. He does like to try on his mother’s heels and necklaces and is an amazing dancer. I see this little guy and smile. I applaud my friend for raising such a charismatic character. Never in a million years do I think anyone should try to change this little creature into something he isn’t. Never in a million years do I think that this little boy at age four is emblematic of who this man will be at age forty. And if there is a connection? He will be an awesome forty-year-old.

Now, I am biased. I grew up an unapologetic no-frills tomboy. I lived for sports. When I was eight and attending soccer camp, I was called “Rambo’s wife” (I was tough and could compete with the boys). I wore a Larry Bird jersey to fifth grade more often than not. And my parents? They let me do my thing. They bought me autographed basketballs for my birthday. They came to my games. And when, in high school, I suddenly started wearing skirts and makeup, they rolled with it. They did what I think a good parent should do (within reason): They stayed out of my way.

But is it this simple? It never is, is it? We parents are doing the best we can. Each and every day. And in each of these days, we are faced with decisions. Some as simple as pink or blue. Some far more complicated, nuanced than that. And so. I don’t pretend to know what’s right and what’s wrong here. All I can do is draw on my own experiences as a child, and now as a parent, in this big, bad world.


  • Do you think we should steer kids toward “gender appropriate” activities and objects?
  • Is there such thing as “gender appropriate” activities and objects?
  • Are there certain toys you wouldn’t let your little girl or little boy play with?
  • Do you believe that we parents should, in many respects, “stay out of our kids’ ways”?
  • Would you have bought your little girl the Diego briefs?
  • Do you agree that the karate school ad was offensive?
  • As a child, did your parents steer you toward certain activities rather than others presumably because of your gender?
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19 Comments for: "Lipstick & Heels On a Little Boy"
  1. I am extremely passionate about staying away from gender stereotyping. Both my little girls love to wear dresses. They also love to play with trucks. They have baby dolls – which they usually end up throwing around or banging on the floor to hear the funny sound a plastic head makes on hard wood. The baby is still too small to have a favorite color – but the toddler loves red. Not pink.

    I think it is terribly wrong to label children, to try to put them in any sort of box, to say, “Oh, you’re a girl who likes trucks so you’re a tomboy,” or “You’re a boy who likes playing dress-up so you’re a sissy.” I even know one mother who gets worried about letting her son help her in the kitchen, because cooking is supposed to be a “girl” thing. (To which I always have the very great urge to point out how many of the best chefs in the world are MALE).

    Let kids grow and develop on their own, pursuing their own interests, encouraging them in finding their own path. My parents let me be a little girl in braids and long dresses, running around playing war with the boys. My dolls and my legos were always set up right next to each other in my bedroom. And I am so, so thankful that they gave me that freedom to be whomever I wanted to be, without fear of labels or condemnation.

  2. It is an intriguing topic. I raised three girls. Although one was a rough-and-tumble tomboy, all three were mesmerized by pink and purple princess accoutrements. I tried to encourage outdoor activity, but the dress-up box held far more appeal than the basketball hoop.

    Now I am helping to raise my grandson. I was curious about this issue, so tried to do all gender-neutral toys. His first word was ball. He quivers with excitement at the mere mention of Thomas the Train, refusing to go anywhere without several engines from his collection in hand. He is obsessed by vehicles of every kind. As a one-year-old, we would sit on the front porch for hours just watching traffic. Per Dr. Phil, I bought a doll to assist in potty training. Grandson doesnt touch it. When his friend, an almost 2-year-old girl, comes to play with us, she wont put it down.

    It has been an interesting experiment. Vive la difference?

  3. I think that while kids will be made aware of gender differences whether through parental guidance, media, or peers, it’s a disservice to force them into choices based solely on the cultural stereotype. It’s a good thing to know when and how to disregard social norms. As a kid, my next 2 sibs were boys, so if I played solo it was with My Little Ponies, with my bros we had the Ninja Turtles or a bucket of rusty nails and old boards for tree fort building. Probably not surprisingly, I favored jeans and t-shirts for a good part of my adolescence, going I think it was 4 years without donning a dress or skirt. The next phase involved makeup and ridiculously high, clunky heels and the occasional purple feather boa in public for no reason. Pretty much a 180-degree change. Testing these norms helps us not only find our interests, but who we are in relation to society at large. If not given the chance to push those boundaries by experimentation, even as kids, I think opportunities to grow as people are missed.

    As for me, I’ve come to a balance. I still wear lots of jeans due to my farm work, which is just sensible, but I have a selection of nice skirts that I like too. (Still have the boa, but it’s more of a Halloween prop than everyday wear now 🙂

  4. I’m totally with you. Kids go through so many phases and by applying shame to any one of them I think we risk doing much more damage than would be done by leaving them alone.

    I do wonder, though, about the greater social acceptability of girls leaning toward boy toys/clothes, than of boys leaning toward more girl things. We are all comfortable with the premise of the little girl who is a bit of a tomboy. She has pluck and spunk (and wears Diego underpants!). We look at Shiloh Jolie-Pitt in her short hair and pirate gear and think she’s kind of a bad-ass (at least I do). But if your fellow underwear-shopping mom had a little boy who wanted princess underwear I wonder if we would view it with the same level of tolerance.

    I guess the question I’m driving at is this: When girls like boy things we assume it’s a phase. When boys like girl things I think that as a society we are inclined to see it as a percursor to something else. Why?

    • Gale, you summed up exactly my thoughts – the double-standard that it’s okay for a girl to be tough, but not okay for a boy to be effeminate.

      • Natasha

        It’s because, as women have come into the sphere of men, we’ve done it to take hold of some of the power that’s long been a part of maleness. We put on the pants and get respect through it. But things simply don’t work the other way around: femaleness is demeaning, so for boys to wear lipstick and heels is derided. Not simply because it’s seen as “gay” – that’s a euphemism for the threat to male power that occurs when boys take on “girly” qualities.

  5. I have a funny story on the topic. A family member and her husband both have masters and/or PhD’s in early childhood education, both have worked in preschools and other schools for years. When they were pregnant with their first child, they purposefully did not find out the gender and they picked a name that would be used whether boy or girl. They talked about their theories on child-raising and specifically said they would not “genderize” their child. They had a girl and her name is a masculine one. It fits her well. Then they quickly had 2 more girls. Both these girls have very frilly, feminine names. I went to their house for the oldest one’s birthday party. It looked like someone had thrown up pink and purple rainbows everywhere. The two older girls had many costume changes, mostly into different colored tutus. I asked my cousin what happened to not “genderizing” their kids? She laughed and said, yeah, that went out the window pretty quickly. They love pink, they are who they are, what can you do?

    Yes I would have bought the Diego underpants, and yes I find that ad disturbing. Like Gale said above, I do think there is more of a worry when a boy shows an interest in girl things. As the mother of a boy, I don’t want him to feel ashamed of what he enjoys or feel afraid to try new things, whatever they may be. But you also have to worry about the teasing. etc.

    It’s a hard question. But I don’t believe that NOT buying the underpants or NOT allowing your boy to express himself will change who she/he is meant to be.

  6. wow. i had not given this a shred of thought until i read your post. jackson shuffles around our apartment wearing my shoes all the time… does the same with my husband’s shoes. the jewelry and makeup has not occurred, but the shoes, most definitely.

    when he’s at my parent’s house, he goes in their closet and wears their shoes, both my mom’s and my dad’s…

    i can’t imagine myself discouraging his curiosity.

    isn’t that what being a kid is all about?

  7. This topic comes up now and then, and I always shake my head, because I honestly think it’s a non issue. In our house, anyway. Fynn totes a leopard print bag filled with matchbox cars to the grocery store. Paige prefers trains over baby dolls (mostly…). They both like elmo undies (regardless of pink or green backgrounds) and watching Dinosaur Train.
    I would probably cringe a little if Fynn wanted pink toe nails, but I’d paint them if he asked.
    I know to each his own and all that, but it maddens me when the gender stereotyping comes into play in any sense. Let them be kids…

  8. First off let me say that anyone who was forced to wear a Larry Bird jersey is in need of severe help. Now mind you, I am an unapologetic Laker fan who loved the ’80s- great basketball.

    Not to mention that everyone knows that the celtics are evil- need an exorcism after watching them. 😉

    On a more serious note, there is a double standard here. Girls can be a tomboy without consequence but the reverse is not true. For a short while the boys can get away with doing more girly things, but there is a point where it can’t happen without problems.

    People can complain about this being unfair and not right- but that is life. Women have their challenges and men have ours.

    So while I am all for teaching tolerance and trying to raise a kinder, gentler nation I am realistic. Some things may lead to problems that we prefer not to deal with or create for our children.

  9. Bravo on the Diego underpants. At least in my view. That exactly what I would have done. In fact I reacted fairly negatively when Grace caught the princess bug (from which she quickly and firmly recovered). I tend to emphasize and praise her tomboy-ish qualities, to the degree that Matt sometimes tell me to chill out. He’s right to remind me to stay mute.
    I will say, having had a boy after my girl, that there are certain things that I assumed were conditioned that appear to be innate. My son grew up with his sister putting pink bows in his hair and wearing hand-me-down pink sleepsacks. No big deal.
    But he also reached for trucks, displayed fascination with trains, and wanted to SHOOT things, in a way that she never did. And I think I’ve been totally the same with both of them, which is to say generally pretty hands-off (to my own detriment: they also both fell down a flight of stairs before they were one).
    I personally think that how we end up is far more nature than nurture, so I think that a lot of the “steering” that goes on is ineffectual at best and damaging at worst, since I think a lot of kids rebel against it.
    My son has a very strong sense of his own style, cares far more about what he wears than my daughter, and passionately loves Mardi Gras beads as an accessory. He also loves trucks, trains, and robots. My daughter is as tomboyish as they get on the soccer field, totally disinterested in clothing, unafraid to get dirty or muddy, and also utterly enamored by Taylor Swift.
    And I am plenty proud of all of those contradictions. All of them.

  10. Amy

    my parents stayed out of my way too…i hated dresses, skirts, and stockings growing up. i never did my hair or thought about playing dress up, with make up, etc. I hit high school and I didn’t even wear eyeliner until 11th grade but when I did, my parents didn’t mind. they left me alone and left me be my tomboy self and when I became a girly-girl, my mom let me use her makeup. haha.

  11. D

    I don’t believe in encouraging children to play with a particular toy. It guts the whole purpose of play- to have fun- if you force your view of fun on them. As other commenters have noted, boys and girls left to their own devices will play with both at one point or another. My daughter is famous for wearing big bow headbands as she plays soccer or runs relay races She is very sporty and girly girl. (she loves princesses but her favorite is Mulan). It is a pretty great way to be but other than my buying her Princess stuff and sporting equipment, I have had little say. With my son, having an older sister meant we didn’t have as many trucks as we did tiaras. So when he was younger he would plop a tiara on his head as he vroom-vroomed his trucks. Now at 6, he is more aware of what girl stuff is from school and from peers and is less likely to play with his sister’s dress up clothes. But now he reads books his sister did like Junie B Jones and the Ramona series which could be construed as more girly. But I can’t imagine steering him in any direction, he is happy and voluntarily reading!

  12. Leslie

    I don’t have kids of my own yet, but I would do what my mom did and let my kids play with what they wanted. When my brother wanted to try nail polish, she let him. When we went to the story and she’d buy us a toy, if I asked for a Hotwheels car, that’s what I got. My brother and sister and I all played with both “male” and “female” toys, and did “male” and “female” activities, and wore whatever colors we liked, and I think we all turned out just fine.

  13. Lori A.

    I say “whatever!”. When my son was born, we already had 5 1/2 year old & 8 year old daughters. There was no chance that he wasn’t going to encounter “girl stuff”.
    He *loved* the Strawberry Shortcake DVD’s we had…would watch them all the time. Not once was I ever concerned.
    Having two older sisters, he has had his share of playing dress-up (including dresses, skirts, etc..I have the pictures to prove it! LOL) and even having makeup applied to his face. At the same time he liked trains and other “boy stuff”.
    Having both girls and a boy, we have visited all sections of the toy store. By choice he chooses “boy stuff”. At 7 years old he’s really into Lego, Tinker Toys, Star Wars, etc.
    It was the same with our daughters. They never really got into what most consider boy toys, but it was of their own choosing. The train set my son plays with is the same set we bought for our younger daughter when she was little.
    I am a middle child with an older brother and younger sister. Having an older brother, I played a lot of the stereotypical boy games and toys..when my sister came along, we started playing more girl stuff. But we were right up there with my brother building tracks for Hotwheels, setting up “war” scenes with army guys and playing Star Wars.

  14. Robert

    Thing is little girls are fre to act and dress and do pretty much what tjhey want without being gender judged as I call it. Let a little boy want to wear frilly silky panties and a frilly party dress and lip stick and he will be said to have issues. A girl is just a tomboy but a boy has issues.

  15. Julie

    People reaally should be better educated. Even the PHDs got educated by their own toddlers. Gender identity is inherent, and not nurtured … that debate died in the 80s. That said, young boys do have a more difficult time in their early years. All children identify with their mothers, and to a lesser degree with older siblings. It is natural for boys then to try and emulate their mothers in their first years, and must make a transition sometime between 3 – 6. Girls not only do not have to make an identity switch away from their mothers, they are given far more latitude in dress and behavior. Girls can wear pretty dresses one day and jeans the next, and play with dolls or trucks.
    Prior to attending school, children should be gently guided to proper gender identity, but never forced. Force never succeeds anyway … so allow children freedom of choice. When it is time for school, the children, unfortunately, then must be taught the rules of societal acceptance.

  16. Kelly

    Natasha hit the nail on the head. Girl dressing as boy is a girl reaching upward in status to reach for male power and status. Boy dressing as girl is a boy giving up the power and status he was given at birth and this threatens all men so this is punished. Tomboy is cute but sissy boy is indicative of a problem in the eyes of too many. Let children be children. Steer them very gently when their choices might lead to peer sanction but if they are willing to suffer the sanctions, then consider that they may be transgendered and get them help in dealing with the people they will encounter who will try to bully or tease them or worse.

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