My Kids Dress Themselves For Picture Day & The Results Are Always Hysterically Perfect

Every fall at drop-off on picture day, I see so many kids dressed in their cutest outfits. Their hair is styled, shoes shined, and clothes dirt- and stain-free, a dramatic change from the feral styles many of these kiddos sport every other day of the year.

My two daughters, on the other hand, stick out from their classmates. That’s because I let my kids pick out their own clothes on picture day. I give them the freedom to choose how they want to be captured... with some hilarious and adorable results.

In preschool, while the other kids were dressed in their cutest holiday outfits, one of my daughters insisted on wearing all black — dress, leggings, socks, and shoes. She was a pint-sized Wednesday Addams among Santa's little helpers. During spring photos last year, my oldest daughter wore a dress with ruffled straps that she intentionally had poking out of a mismatched cardigan. She looked like the cutest little mess there ever was.

As an adult, looking back on my school photos makes me laugh (and, OK, cringe), because I changed so much from year to year, and that’s what I want to see when I look at my kids’ pictures, too. When they’re all grown up, I want to have 13 years of awkward photos that remind me of who they were throughout childhood, and to me, there’s no better way to accurately capture their personalities than by letting them choose their own clothes and hairstyles. I strongly believe that what we wear and how we style ourselves is a form of expression, and I don’t want my daughters to hold back.

So far, this approach has worked out exactly as I had hoped. For instance, when my oldest daughter was in kindergarten, she insisted on wearing a bright, summery dress (even though these were fall pictures), a huge JoJo Siwa bow in her hair, and a princess Aurora dress-up costume necklace. This mismatched look combined with the “sparkle” background she chose and her proud smile speckled with missing teeth is exactly how I want to remember her at that age. It’s only been two years since that photo, and her style and personality have already changed so much.

I love school pictures. Are they overpriced? Absolutely. Are they worth the money? Yes, every single cent. There is nothing else like them. Those cheesy backgrounds, the strained smiles, the lighting that’s always just a little off. School photos are iconic, and I want my kids to be as pumped up about their pictures as I am now.

I’ve always loved picture day. When I was a kid I spent so much time carefully choosing what I would wear and how I would do my hair. In elementary school, I was always wore some kind of floral print, and there's no way to describe how glamorous I felt with my big bouncy curls courtesy of my mom's hot rollers.

There was so much joy in the anticipation of getting the proofs back, and when the finalized order arrived it was like the school version of Christmas morning. I’d eagerly open the envelope and cut up the wallet-size pages my mom would order for me every year, then proudly pass my portrait out to my friends to be hung up on their locker doors like the elementary school versions of a MySpace Top 8 page.

In the age of iPhones and a camera roll full of pictures of my kids, I genuinely cherish their school photos in a way that I never anticipated. I even order the physical printed out for us so that they don’t end up lost in a folder of digital pictures labeled “To Print” that I never get around to actually printing. Those silly photos deserve to be framed and displayed prominently in our home, and I will not be convinced otherwise.

If you’re a parent of one of my kids’ classmates who longs for a class photo full of polished, smiling students for your and your child’s memories, I apologize. I know could give my daughters some parameters on school picture day, but I don’t want to. If one wants to wear a pink sequin dress, I will let her. If the other insists on wearing a headband with cat ears, I’ll make sure they’re straight and give her an encouraging high-five before she walks into school. I want their school photos to be totally authentic, and there’s nothing more genuine than my kids’ chaotic energy and self-expression.

Ashley Ziegler is a freelance writer living just outside of Raleigh, NC, with her two young daughters and husband. She’s written across a range of topics throughout her career but especially loves covering all things pregnancy, parenting, lifestyle, advocacy, and maternal health.