Motherhood gives rise to various lose/lose situations over the years, with fashion responsible for more than several of them. Surely you can name instances of blaming your mother, “You never let me me wear what I wanted” as well as “I can’t believe you sent me out of the house like that.” My own recollections include Doc Martens (the former) and a certain Dorothy Hamill bowl haircut (the latter). Other questionable trends you might recall with nostalgia span feathered bangs, leggings with scrunchy socks and acid-washed denim jackets. And at the root of each missed opportunity and every regrettable outfit was your mom.

Just for a moment, though, let go of that hostility and step into her Keds shoes. It’s harder than it looks to guide your children through a world of constant and harsh judgment. It’s even harder on those of us whose kids have unconventional predilections. As a mother of two children who are each in their own right out-of-the-box thinkers and doers, I’m ever balancing my conflicting maternal instincts– one of which urges me to protect their vulnerability and the other to nurture their individuality.  To this end, Halloween is particularly stressful.

Spooky in origin, Halloween is actually a creepy night when wallflowers will transform themselves into Slutty Snow White and mansie-pansies into suave Magic Mike. Others perhaps are dripping with gore, or feigning super power.  People let loose, celebrating not who they are but who they could be when inhibitions disappear. They explore the other-worldly on a night when all limits are off.

Or are they?

Some lines just shouldn’t be crossed, such as when Prince Harry emerged as a Nazi. That was simply dumb. Others are more innocent. Cue my son, who makes a darling Merida this Halloween season. If you haven’t seen the movie Brave, you must, if only for the animation of Merida’s wild, fiery hair. Ironically, this was my son’s big draw to the character but now he doesn’t want to wear the defining wig. Herein lies the conflict. Clearly he is a boy in a dress, but with the wig, it’s less obvious. Protected by the wig his gender may go unnoticed as he parades around his new 1,000+ person school, complete with preschool-aged kids up to high school seniors. Without the wig, all bets are off. He is a boy in a dress.

Personally I have no problem with this. I am a woman who prefers to wear pants. This too used to be criticized and jeered– and not so long ago. It now sounds so silly doesn’t it?   I wish you’d all agree that pants and dresses don’t determine our worth as individuals, but that’s a naive request. For some reason not all of us are there yet. Articles celebrating gender creativity appear from time to time, each of which resonates profoundly. The most recent of note, from The New York Times Magazine (August), poignantly highlights boys wearing dresses.

Like several articles before it, this tells the stories of children living life unconventionally and parents supporting them unconditionally. Wouldn’t you do that for your child?

My mother thought she was doing right by the bowl haircut. I can assure you that it was wrong. So very wrong. Time will tell whether my purchasing the Merida outfit will be valued or resented. For now, what I can say with absolute certainty is that there are things much more twisted on Halloween than a boy in a gorgeous turquoise dress. Funny how if we are so concerned with what a child’s disguise implies about his or her future behaviors, decisions and lifestyles, that we condone– celebrate even– the blood-lusting, weapon-wielding, terror-seeking figments of horror portrayed by the conventional boy’s costume. I’d take unique over depraved any day. We witness too much violence in the world already. What we need to see more of are the awe-inspiring characters who encourage us all (and I write this in my best Scottish Princess voice) to follow our hearts… to write our own story.

So when you see him, my brave boy, this Halloween give him a cheer. And maybe even an extra piece of candy for his mom. She deserves it.