When I was a kid, every school year would start out the same: an obligatory photo in the driveway, locked in a forced hug with my sister, both of us dressed in what can only be described as cult-core chic. And because words don’t do it justice, the picture is below: floral maxi dresses layered over t-shirts and white Keds. It was the late ‘80s/early ’90s, and while trends were questionable, even by those standards, this was a choice.
Fast forward to my daughter, who somehow mastered style before she could spell it, leaving me decades—and several bad outfit choices—behind.
Last year in third grade, my daughter had OOTDs lined up like she was waiting for her close-up in Vogue Kids. Meanwhile, I’m out here looking like a cautionary tale from a What Not to Wear rerun. I found myself constantly reminding her: Not everything is a fashion show. Her response? “Oh, but it is.” Cue the dramatic eye roll—hers and mine.
Of course, the first-day-of-school photo tradition is non-negotiable. It’s the one parenting ritual that’s equal parts sweet, sentimental, and, let’s be honest, an unspoken competition on Facebook.
When my kids were in private school, this was blissfully easy: uniforms. Everyone looked polished, and my only job was to make sure their hair wasn’t sticking up in seventeen directions.
But when we switched to public school last year, I got ambitious. I invented what I called the “mommy uniform” – chino shorts or pants and a collared shirt for the boys, a dress or skirt with a semi-nice top for my daughter. Jeans were acceptable. However, no sweats, no athletic wear, and no stretch pants unless they are layered under something else.
Spoiler: my “mommy uniform” lasted until about March. After that, I surrendered. Wear whatever you want, just please get out the door and to the bus on time.
This year, I thought I was being smart. I set the bar low: two rules: one, no stains. Two, look nice for the first day. Apparently, even that was controversial. My daughter came downstairs in a crop top and short shorts, tossed me an Olympic-level eye roll, and shrieked, “WHAT?!” with all the drama of a Shakespearean tragedy. Not happening—not even when “looking nice” isn’t on the agenda.
My middle son’s choice? Athletic shorts and a shirt that looked like it moonlighted as a napkin at Olive Garden. And then there was my youngest: completely naked, standing before drawers bursting with clothes, declaring with great conviction that he owned “absolutely nothing to wear.”
And that’s when it hit me: every September, we’re not just wrestling with kids over outfits, lunches, and bus times. We’re also wrestling with the ghosts of our own school days—the awkward pictures, the questionable fashion, the memories we can’t quite shake. Every outfit argument with my kids is, in some way, a tug-of-war with that driveway photo from 1991.
But here’s the thing: maybe those ghosts are supposed to follow us a little. Perhaps they serve as a reminder that the photos don’t need to be perfect, the kids don’t need to be polished, and the memories aren’t meant to be curated. The truth is, what makes those old pictures so hilarious now is exactly what will make today’s photos so precious years from now: the cringe, the chaos, the “what were we thinking?”
So yes, my daughter will probably roll her eyes at me every September. My son will try to pass off ketchup stains as “abstract art.” And my youngest will keep insisting he has nothing to wear. But maybe that’s the point. Someday, they’ll look back at these first-day photos and laugh.
And maybe, just maybe, they’ll see that the real tradition isn’t about the clothes at all—it’s about standing in the driveway, together, at the start of another year.
Even if you look like you just stepped out of a cult brochure.
