I grew up in Maine, where trick-or-treating was often a frosty affair. My mom would insist that snow boots looked perfectly fine with Cinderella’s ballgown, and that Frankenstein was still totally scary beneath a puffy down coat. My kids are growing up in South Florida, where I wage the opposite battle. Every October, I pitch costume ideas that involve shorts. “How about a boxer? I can give you a fake black eye! Or a lifeguard. You can wear a whistle!” This never works. Our first year here, my boys dressed as Power Rangers, in full-length polyester suits. They got so hot on the walk home that they stripped down to their underwear. Another year, they were Indiana Jones (cargo pants, long-sleeved shirt) and his greaser son, Mutt (jeans, “leather” jacket). That was an especially sweaty Halloween. (Faux leather does not breathe. AT ALL). This year, the boys plan to be Batman and Robin. Come on….wouldn’t some nice cotton shorts look perfectly fine on the Dynamic Duo?
When Sam was three, “fairy” was the Halloween costume of choice. Many trick-or-treaters mistook Sam for royalty. “What a pretty princess!” they exclaimed. “I’m not a princess,” Sam snarled back. “I’m a fairy!”
The funny thing was, no one considered he might be a boy.
At six, Sam startled us by wanting to be Luke Skywalker. Given that we’d never seen him express interest in a masculine costume, we didn’t know what to think, except that Halloween is a time for experimenting, trying on new identities, or being things we are not.
Each year, pink boys wonder: If I wear the costume I want to, will the kids at school make fun of me? The parents of pink boys wonder: Is this safe? Can—should—we trick-or-treat somewhere where nobody knows us? Of course there’s no “right” answer; each family has to work out on their own what works for their child. If this is your family’s struggle, we recommend a video from The Onion, America’s favorite satirical news outlet: “How To Find A Masculine Halloween Costume For Your Effeminate Son.” It won’t answer your questions, but it will help you laugh about them.
Dressing up like pirates was always a fun costume choice when our two boys were small. From store-bought accessories to homemade ones, there were so many options. Eye patches, hats, bandanas and more! School parades and trick-or-treating were lots of fun…but the fun didn’t end on the last day of October for us.
Costumes and accessories were added to a laundry basket designated as “dress-up clothes.” Kept right next to all the gadgets and gizmos of childhood, the items in this basket were played with almost more than any other toy we owned. I loved the imaginative play it encouraged. Our kids loved it for all the exciting moments they had.
They’d play “dress-up” and re-enact favorite stories we’d read. They’d pretend to be a pirate or a dinosaur or an astronaut (Yes, we had a dinosaur and astronaut costume, too!) or “fly” around the house wearing a cape made from a large scrap of fabric. Many family memories were made—all from playing “dress-up” the whole year round.
When I think of Halloween, I think of my right ankle. I broke it three times: in first, fourth, and sixth grades, each time right before Halloween, a holiday where ankles really come in handy for trick-or-treating.
The first time my brother John told the neighbors about my injury and they compassionately dispensed sympathy treats. The second time John was with his fifth-grade cronies and didn’t want to seem uncool, soliciting candy for his clumsy kid sister, though some of the neighbors kicked in an extra candy bar. But the third time we had just moved to a new neighborhood where no one knew us and John volunteered nothing, so no one knew of my candy-less plight.
That night John came home to me lying miserably on the sofa and the guilt kicked in. He gave me the candy he didn’t like, basically anything with peanuts. This brings me to my second, happier Halloween memory: Snickers. Years later, when I took my own kids trick-or-treating, I would relive my youth by coaxing them into sharing their Snickers bars, insisting I deserved something for walking with them for hours. I’m happy to report guilt worked, just like it did on John.
I turned 15 years old on Oct. 19th. This was the first year I started to feel a little old for Halloween — a favorite holiday for my best friend Lori and I since we shared October birthdays, too. I wrote in my diary at the time that John, a boy I crushed on, went trick-or-treating with us that year. Lori and I always had so much fun making costumes and walking out in our friendly neighborhood to collect candy. Afterwards, to avoid eating TOO much candy at once, we made a game of hiding our wrapped candy in our bedrooms. We’d usually forget where we hid it, making Halloween last a long time.