A Princess for a Day: Should You Let Your Son Don a Dress for Halloween?
Halloween is a time when kids stretch their imaginations, but is a double standard at play if girls can be cowboys but boys can't be princesses?
Amy Ettinger, Contributor
Articles> Holiday Activities and Tips> A Princess for a Day: Should You Let Your Son Don a Dress for Halloween?
girl in princess costume

You're shopping for Halloween costumes with your 4-year-old son when he announces he wants the white taffeta princess costume with the tiara. Do you grab it with a smirk thinking of how he'll look back on this when he's 30? Or, do you ignore him and pay for the blue and red spider man costume you planned for all along? On the one hand, it could mean years of therapy if you let him pretend to be a girl for a day. On the other, it's all about make-believe, so shouldn't kids be what they want to be?

Playing dress-up is more than just fun. It also teaches creativity and allows children to role-play. Halloween is a time when kids stretch their imaginations. But many parents say there's a limit to how far they'll let their boys go. Care.com recently ran a poll asking "Would you let your son be a princess for Halloween?" The overwhelming response was "no," with 65% of readers saying they would not let their son put on a dress, and 35% saying they would. The results were flipped when the question came to girls dressing up as boys. When we asked "Would you let your daughter be a cowboy for Halloween?" 90% of readers said "yes" and only 10% said "no."

What accounts for these lopsided results? Meg Meeker M.D., bestselling author of six books including "Boys Should Be Boys: 7 Secrets to Raising Healthy Sons" says parents often sexualize their kids dressing up, although their children don't connect clothes with sexuality.

Meeker says that parents need to allow their sons to explore different types of play including dress-up since that's how children learn about their role in the world.

"Boys might want to see what it feels like to act like the mommy or the princess or the witch," says Meeker. "We need to allow our boys some freedom."

If a boy wants to dress like a girl, "it isn't a statement about the child's identity or his future sexual identity," Meeker says. "It's child's play."

Is the World Ready?

It seems society still stigmatizes boys who want to raid mommy's closets. Last year, blogger mom "Nerdy Apple Bottom" received an overwhelming response after she posted a photo of her 5-year-old son dressed up as Daphne, a character from "Scooby Doo." More than 45,000 people wrote into her blog, praising her decision to let him gender-bend, while others trashed her parenting style. On CNN, a clinical psychologist, Dr. Jeff Gardere, accused her of "outing" her son by posting the photo on the Internet.

Dr. Robi Ludwig, Parenting Expert for Care.com and nationally-known psychotherapist, suggests that boys who want to dress up as girls be encouraged to do so at home instead of in the public sphere. Ludwig says it makes much more sense to allow children to dress-up far away from other children or parents who might tease or torment.

She adds that some parents react with strong homophobic feelings when they see their boys in drag. Boys who express an interest to dress up as girls should be allowed to do it, but considering the mockery and potential damage this playfulness might have on his ego, Halloween is probably not the best time to experiment.

As for girls, they tend to get more freedom when they decide to dress up as a cowboy or prince. It may be because women can wear pants without reflecting sexual orientation. "It reflects our cultural and gender biases," says Ludwig. "There's still a double standard."

Getting Everyone on Board

When Katie Bugbee of Newton, MA recently hung out with friends, her 3-year-old son came up from the basement playroom in full princess garb. High heels, jewels and all. "He had been downstairs playing with some older girls and was so proud of himself. The only thing I could do was share his excitement," she says. Her husband was immediately on the same page, giving the appropriate oohs and ahhs. "You could tell everyone was watching for our -- and especially my husband's reaction. But sharing in his happiness made it less of an event." For the next few months, her son talked about being a princess and Bugbee had to make sure her nanny and parents never made him feel shame. "He has his whole life to learn what the world expects from men and women. The only thing I can assure him is that his home is a safe place for whatever he wants to do or be."

Dr. Ludwig says the best strategy is to educate everyone involved with the child including spouses and babysitters. "It's important not to impose gender ideals at this point, but to observe their natural tendencies and to be loving during this exploratory process," she says.

Considering there may be cultural or generational differences when explaining this role-play, she suggests telling caregivers, "Ben loves playing dress-up right now and calling himself a princess. We're not discouraging it and want to make sure you treat it like it's completely normal. We don't want to make him feel any shame. Are you okay with that?"

Sharing and and Supporting

Author Cheryl Kilodavis has written a non-fiction picture book called "My Princess Boy," the story of a four-year-old boy who likes to wear a dress and jewelry. The book is intended to start a conversation about unconditional support for children and how they wish to look.

Through her website, Kilodavis has inspired 50 "acceptance groups" across the country, meeting in children's playrooms, including some provided by members of the Episcopal Church.

"The goal of acceptance groups is to provide families a safe place to connect with each other in their own neighborhoods and to have conversations while modeling how to accept differences," said Kilodavis.

These families also gain access to a secure website where they have can ask personal questions and start deeper conversations about their children's lives. Kilodavis hopes the groups will expand internationally.

"We have children representing many differences -- cultural, religious, family make up, princess boys and emperor girls," she says. "The one rule is to accept each other as is."

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(11) Comments
Cathy Laura Peterson
Cathy Laura Peterson
I also agree that there's nothing inherently wrong or harmful in letting our sons have a little fun on Halloween. I think if we make it an issue, it then becomes one, but if we simply view it as creative expression for one day (not permanent), then everyone can be at ease and go with the flow.

My 2 daughters and I dressed up my son/their little brother (he's 6 1/2) in a cute frilly party dress, complete with ruffled rumba panties, lace white tights, black patent leather buckle shoes, and 2 layers of poofy lace slips underneath (one full slip and one half slip). We put his hair up in plastic bow-barrettes, did some nail polish, and took him to our church's Halloween party and we all had a lot of fun, and he was very happy doing all the game booths and no one was weird out about it.

On the other hand, last year I helped my sister's oldest son (age 15, my nephew) with a very "authentic" girl costume for his high school Halloween fair and dance. He's 5'7" and very slim (boney) build, has shoulder-length hair, fair skin, skinny legs. Well, it was obvious that anything we did with clothes, hair-styling, make-up, jewelry only made him look even more and more like a real girl, so we all had a few laughs early on with going 75% "girlie" ideas and finally decided to do a 100% costume and see what happened.

He was a real sport about it all, as we flat-ironed his hair then did a gorgeous French-braid with long feathery bangs in front. By the time we finished his make-up (oh my gosh he has such long natural eyelashes) so we did very light foundation (he's got flawless smooth-clear skin) with pink lip gloss, deep maroon + gray smoky eye shadows, black eyeliner, and 3 coats of thick black mascara, added a necklace and clasp dangling earrings - well let's just say there was NOTHING left of that 15-yr old boy. He was actually very "pretty" even by girls' standards.

Well his sisters (my nieces) his mom and I and my girls all pressed him to "just go for it" so he wore a padded push-up bra, a control top high-waisted shaper-panty (so he was completely flat in front between his legs), nude lace-top thigh highs, 2" heel black pumps, an old Vanity Fair pink nylon full slip, and then a gorgeous rayon-crepe light pink dress my sister wore to a wedding about 10 years ago. It fit him perfectly, like it was tailored for him, and was such a complete visual illusion as the thin dress showed his bra and slip straps and lace accents thru the thin fabric. We added pink nail polish, bracelets, rings, perfume, an ivory silk scarf with little pink roses, and a black leather shoulder purse. I do think we went WAY overboard on the poor guy once we got started and couldn't stop adding to his "look".

Well, he was so completely over-the-top 100% authentic in his female look, that he actually looked more like a college age/20-21 year old young woman - and while we were the ones who pressed him to do more and more getting dressed, it was a little weird when after he was completely dressed, it shifted to him REALLY getting into it, maybe a little too much??!

Rather than acting silly, or like a guy in a costume, my nephew seemed to slide deeply into a very feminine manner in how he walked, and he softened and raised his voice when he spoke (which sounded very much like a gal), and it was only around 2pm when he was all finished up, but he wanted to go out and walk around, which led to a few smiles and laughs and dares from the other gals, and soon we were all on our way to a large mall near our house to walk around and shop.

As me, my sister, and 4 of our daughters plus this 5th "young lady" walked across the parking lot to the Macy's front doors, it was a little creepy that he was SOOOOOOOO into walking like a girl and walking arm-in-arm with his cousins, and from behind I just saw 5 young gals and it was so hard to realize that the one in the cute pink dress was my nephew, especially seeing the 2 sets of straps over his shoulders and the lacy back of the full slip over the bra's back-band ALL peeking thru that thin dress. His legs looked amazing, all smooth and in nude stockings, and I was shocked to see how easily he walked in those 2" heels.

I won't' give the entire details, but we were there almost 3 hours, during which he went to the make-up counter at Nordstrom and a woman did some touch ups on his make-up with NO idea at all he was a boy, as they all took turns and were now calling him Carly.

He even tried on skirts and tops in the changing room with his sisters and cousins at Forever-21 and Old Navy, and there wasn't a single hint that he wasn't just one of the 5 girls shopping together. We got fro-yo in the food court and he sat with us like a little lady and talked with his girl voice, and my sister and I were both a bit concerned that we'd NEVER seen anything like this in him at all, and maybe he was a bit TOO into this??!!??

He went to his school's party and dance that night, and apparently it was both fun and a bit awkward as many teachers and students made comments about how much like a real girl he looked and acted. So let's just say my sister had quite a time talking him down when he got him at 1am and wanted to hang around and watch TV in his lingerie and dress.
November 3, 2014 at 12:34 PM
There is nothing wrong for a boy to dress like a girl for Halloween and if he wants to dress like a girl on other days so what? Maybe he is transgender. There's nothing wrong with that. Parents that suspect thier child is transgender should take them to a gender clinic or a counselor that deals with transgender youth. You need to support your son and not suppress his feelings. Parents need to be understanding and compassionate. Transgender children do exist and they are the happiest when they can feel secure with their parents. Children shouldn't feel ashamed to express who they are. Sylvia says boys "Should" be boys and girls "Should" be girls. Sylvia needs to understand what transgender children are all about. She needs to educate herself on the subject of transgender youth and transgenderism in general and to be more compassionate and understanding. The comment Sylvia left is like saying men who are gay "Should" NOT be gay and lesbians should "NOT" be lesbians. You can't change what nature has dealt. So if a boy wants to live as a girl he should be allowed and not be shamed by the parents. The same goes for a girl that wants to live as a boy.
September 12, 2014 at 4:22 AM
Mom of a princess boy
Mom of a princess boy
Sylvia W.....Get a life! It's 2013 and things are a lot different now then when you were growing up back in the 40's/50's!
November 2, 2013 at 1:07 AM
Corrie F.
Corrie F.
I'm all about children "feeling safe" in their own home while they explore their likes and dislikes.
October 25, 2011 at 10:40 PM
Sylvia W.
Sylvia W.
When a boy wants to dress like a girl, the adults should use that time to help him learn that there are male roles that are he can follow. Boys should be boys and girls should be girls. If the parents hve been proper role models from birth then it is very unlikely this delima would occur. My husband and I raised 3 boys to be MEN. They were taught that God had a special purpose for their life, and that was to be a MAN that honoured God.
October 25, 2011 at 3:03 PM
Sarah D.
Sarah D.
These strict gender roles and double standards are the reason why its still difficult for men and women to be viewed as equals. I expected it to come from fathers, but I know lots of mothers that would not allow their sons to participate in any activity that may be viewed as feminine, in the fear that it may encourage them to become gay. I cannot believe that people can think that!
October 25, 2011 at 8:50 AM
Fatoumata D.
Fatoumata D.
i like to with u guy
October 22, 2011 at 2:45 PM
Jennifer L.
Jennifer L.
who cares kids are kids do you really think a five year old will grow up to be gay just because he put on a dress. I was a live in nanny for years and one little boy in particular used to love to help me paint my nails and often asked me to do his toes. This was when he was two by the age of five he would have rather eat spinach than help me do my own toes, let alone his, because it was "for girls". Kids will feel the pressure of society soon enough let them enjoy themselves in the safety of their own home while they still can.
October 13, 2011 at 8:23 AM
Kayla G.
Kayla G.
I think if it's what the boy wants, let em go for it. You don't see Parents freaking out over their little girl wanting to be a cowboy or any other boy costume, it's only when boys do something "different" that it is wrong.
October 6, 2011 at 4:51 PM
Anna C.
Anna C.
Hello. The parents can always visit the Irish/Scottish culture. Irish/Scottish Kilts could be the alternative for any boy.
There is quite a bit of information on the web including pictures.
Good Luck!
September 28, 2011 at 1:07 PM
Michelle B.
Michelle B.
what is so wrong with having a little boy be a prince and a little girl be a cowgirl? ???
September 27, 2011 at 5:03 PM

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