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?

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."

Like this? Get more. Sign up for the latest articles, news and tips of your choice. All delivered weekly to your inbox.
Enter your email address:
Comments (9)
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!
Posted: November 02, 2013 at 1:07 AM
Photo of Corrie F.
Corrie F.
I'm all about children "feeling safe" in their own home while they explore their likes and dislikes.
Posted: October 25, 2011 at 10:40 PM
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.
Posted: October 25, 2011 at 3:03 PM
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!
Posted: October 25, 2011 at 8:50 AM
Fatoumata D.
i like to with u guy
Posted: October 22, 2011 at 2:45 PM
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.
Posted: October 13, 2011 at 8:23 AM
Photo of 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.
Posted: October 06, 2011 at 4:51 PM
Photo of 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!
Posted: September 28, 2011 at 1:07 PM
Michelle B.
what is so wrong with having a little boy be a prince and a little girl be a cowgirl? ???
Posted: September 27, 2011 at 5:03 PM
Leave a Comment
You can post a comment by logging in to your Care.com account or continue as a guest below.
Display Name*
Success! Your comment is waiting to be approved. It will post soon.
Post another comment

Connect with Care.com

Join Free Today!
What would you like to do?
Membership Type*
By clicking Join Now, you agree to our Terms of Use and Privacy Policy.
Put Safety first
Read our Safety Guide for tools and tips to keep you and your family safe.
Visit Sheila's Blog
Get advice for your family from our founder (and chief mom officer), Sheila Lirio Marcelo.
Sponsored Listings