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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?

A Princess for a Day: Should You Let Your Son Don a Dress for Halloween?

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. 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 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.”