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Should I Let My 5-Year-Old Son Be a Princess for Halloween?

Photograph by Twenty20

Halloween is cosplay for 5-year-olds. My son has a costume collection which rivals that of any Comic-Con goer. Lately, I doubt I’d recognize him if he weren’t dressed up as "Aladdin" trying to clothe our dog as his sidekick monkey. Clearly, Halloween is a favorite holiday and finding the perfect getup is a must. This year, the quintessential costume has yet to be discovered, but once it’s found, I’m sure I’ll be his usual fairy godmother providing him with said perfection.

“Mom, can I be a princess for Halloween?”

Oh. I wonder if I can bibbidi-bobbidi-boo glass slippers in his size?

Our costume bin does not discriminate. There are fireman hats mixed with pink tiaras, and Captain Hook pants juxtaposed with "Vampirina" dresses. There are no boy/girl stereotypes when my son plays dress-up because playing dress-up is exactly that: play. I’ve always encouraged him to explore his creative side and have fun in the process. This is why my son’s request to don a shimmery princess gown isn’t that much of a shocker. He’s at home in a world where boys can cross over into the girls' section without bias. And why not? We girls do it all the time. Back in the day, Katharine Hepburn wore pants, so in this day I can wear pants and not get arrested. Still, is the world ready for my little guy to trick-or-treat in a princess dress?

If someone decides to judge my son because he’s wearing taffeta instead of denim, then we will deal with that together.

I have no problem with my kid playing dress-up in a myriad of different colors and styles, but others might. Boys in princess dresses are not the norm. I want to keep his heart safe from the possible negative fallout of his choice, and this situation is a hard one to predict. In my Halloween nightmares, I hear mocking giggles and biting whispers following him down the crowded costumed streets. My worst fear is that others will pay more attention to his unusual getup, forgetting about the little boy’s feelings inside of it.

My son’s heart wouldn’t be the only heart that would end up bruised from a scary night of trick-or-treating. I’d be wrecked if people’s judgment hurt my kid when I could have stopped it from happening. Would the fun of Halloween be ruined by the disapproval of other trick-or-treaters? I could just tell him that he can’t wear a dress. I could try to suggest a more “boy-like” costume like a cowboy? (He can borrow my boots—although they might be a little big.) Should I let my son be a princess for Halloween?

If my son’s final spin of the Halloween costume wheel lands on “princess dress,” he will have my approval. His heart is still growing and assimilating information, and one piece I definitely want him to have is that his mom will be there to high-five his creative choices.

Halloween is a day when we’re all allowed the freedom to dress up as we choose. If he wants to have fun in a dress, let’s do it! If someone decides to judge my son because he’s wearing taffeta instead of denim, then we will deal with that together. So, if my son wants to be a princess this Halloween, I will be there to hand him his tiara.

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