When Elliot, 3, said he wanted to wear his purple and white tie-dye dress to daycare, his father wasn’t sure this was such a good idea. It was one thing to wear it at home, or concealed by a coat when he went outside, but how would his daycare buddies respond?

“I think I do a bit more of the worrying,” says Elliot’s dad, Nick Gamble, of Toronto. While Elliot did wear the dress to daycare, and the teacher mentioned that no one had made any reference to it, that didn’t completely alleviate Gamble’s concern. He wondered, at what point do kids start to become judgmental? And do we want to wait until he gets called a sissy before he gets the message to stop wearing it?

It’s hardly unusual for little boys to try on their mother’s shoes. Nor is it unnatural for a boy to ask for sparkly nail polish, or to want to have his hair in a pigtail. But when does our preschoolers’ playful “cross-dressing” at home become less desirable behaviour in the outside world? And why shouldn’t boys be able to express themselves? Here’s what the experts have to say on the topic.

what makes boys want to dress as girls?

“There are as many reasons as there are children,” says Barbara Lis, a Montreal-based psychiatric social worker. He could be expressing his warm nurturing side. He may want to be like his sister. Or as Rosemary Carlton, a Montreal doctoral student with experience in the social work field explains, he may simply enjoy certain colours or textures. “Some are aware of the connotation of dress. Others are not.”

“It’s healthy for children to explore different parts of their personality,” says Lis. That may mean dressing up as a fireman or a ballerina as a way to try out different attitudes and behaviours. As for whether it is an indicator of later sexual orientation or gender identity, Cory Silverberg, a certified sexuality educator in Toronto, says, “There is no compelling and balanced research addressing the relationship between cross-dressing at a young age and identifying as transsexual or transgendered later in life.” Because cross-dressing is a predictable and healthy way for children to explore gender roles they perceive in the world around them, Silverberg contends that it’s impossible and not very helpful to try and guess what it means.

how long does this phase last?

Lis says that parents report a decrease in this behaviour around ages five to seven, at a time when the child may be “identifying with the same-sex parent, when he has a better-developed sense of self, and is getting messages from peers, family and school about what is appropriate and what is inappropriate.”

can this behaviour become a problem?

“Even if the adults are ready to challenge stereotypes, I’m not sure the kids are,” says Carlton. “Kids are incredibly susceptible to expectations of how they should look and dress or behave, and gender stereotypes are rampant in schools.”

If your child’s desire to be or dress as the other sex is causing him inner conflict, you may want to get a referral from your family doctor or turn to local outpatient departments for child psychiatry that can direct your family to more specialized services; they may be able to assess the “strength of an impulse” by observing the frequency and intensity of the behaviour and his ability to voluntarily engage in other activities. And of course talking helps, if the child has the words to express what is going on for him.

Diana Ballon is a Toronto writer whose inspiration for this story came from seeing her three-year-old son dressed in his sister’s pink tutu.

best ways to respond

1 Validate the child’s feelings. “Focus on his self-esteem,” says Lis. It’s important not to discount the child’s tastes or interests, nor send a message that the child is in any way flawed.
2 Establish boundaries on his behaviour. For instance, you could say, “In school, boys wear pants. At home, you can dress the way you like,” Lis says. If you are struggling with whether or not to let your son wear a dress to school, Carlton suggests talking to the teacher first to gauge how he or she responds, and how the teacher feels his classmates might react. If the teacher thinks it’s weird, it’s unlikely that your child will feel safe, says Carlton.
3 Encourage healthy exploration. If you have a dress-up box at home, make sure it has a whole range of make-believe alternatives in it, says Lis. A superman outfit. A dress. A wig. A fireman’s hat.