View our other publications:

Loony fashion

Toddler style for the win

As she hopped off the city bus into stifling heat, my mom looked down the street and let her eyes adjust, trying to confirm that what she saw was real: her husband and three children galloping toward her in questionable outfits, looking like an Insanity Quartet. There was fabric flying where fabric shouldn’t be. As our designated stylist, my mom noticed immediately that we were not wearing the clothes she left out for us that morning.

With mom at work, our dad was left in charge today, and we all knew what that meant: Normal routines were much looser. Compared to the detailed planning my mom leaned on to keep everything running smoothly, Dad was more of a bottom-line guy: are the children alive and in one piece? Yes. Well then, mission accomplished. 

Before she left for work, my mom picked out outfits for me, four years old; my sister, two and a half years old; and our baby brother, coming in hot at nine months old. Mom learned quickly that my dad was not cut out for wardrobe consulting.  Earlier in the year she set out two sets of clothes for my day at preschool: one if it was chilly and one if it was hot. By the time she picked me up from school, I was a sweaty mess. She started investigating and discovered that my dad put me in BOTH sets of clothes. He even went to the trouble of putting my socks on underneath my stockings, stating that he knew my mom was “picky about that stuff.” From then on, mom made every effort to ease the burden of getting three unruly toddlers dressed at the same time. That day, she even laid out socks and accessories, but with Dad at the helm, all sartorial hell broke loose. When The Stylist’s Away, The Aspiring Fashionistas Will Play.

First, we’ll tackle my coup: There was a heavy, lace-adorned dress at the back of my closet that I had been eyeing for months. It was three sizes too big, but my mom stored it there for when I finally grew into it. Without my mom around to stop me, I pulled it from the reserves and gleefully put it on. The lace was too heavy for the summer heat and was more appropriate for, say, dinner with the queen than for watching cartoons at home. But I was not about to let logic pull me away from the fashion fast track.

We now turn our attention to my sister’s tantrum. She spotted the green corduroy overalls laid out for my brother and lost her mind. The overalls used to be hers; once she outgrew them, they were handed down to my brother, who was now baby du jour. Since they were her favorite overalls, she wouldn’t let them go without a fight. Rather than put up with her histrionics, my dad relented, and my sister reclaimed her pants. Baby bro is out of luck.

Already exhausted from dressing us, my dad announced that it was time to go to the bus stop to walk my mom home. My sister and I were pumped to show off our fashion victories and happily bounced out of the house. As the bus pulled up, we waved and ran toward my mom, who was befuddled by what she saw:

I led the pack, flapping my arms up and down as my lace parachute fluttered aggressively in the breeze. There was so much fabric flying that my mom worried I would lift off the ground and float away. That couldn’t happen, though, because I was anchored to the sidewalk with a chunky pair of Winnie the Pooh boots. Winnie the Pooh winter boots. In the middle of July. Lest my ankles get too hot inside the wool lining of said boots, I shielded them with a pair of teal green striped knee-highs that I stole from my sister Brooke’s closet. Brooke was a teenager, I was enamored with her wardrobe, and I sneaked into her closet and stole things at every turn. Brooke, being older (and taller) than me meant that her socks reached up to my waist, which only added to my confused aesthetic. I skipped toward my mom in a bubble of euphoria; a child who knew they’re hitting all the fashion high notes. 

A few yards behind me, in a more labored strut, was my sister. Being that she had long outgrown the baby overalls she insisted on wearing, the inseam and bib straps did not accommodate her height. As she walked, she bent over at a forty-five-degree angle. The impaired gait didn’t bother her though, because she was buoyed by the confidence of a mercurial toddler who knew she’s won her battle—and that’s what really matters. 

Closing out the runway of this deranged fashion show was my poor, outgunned father. He is battle worn, but his job was done: All the kids were alive and dressed. Well, almost. Don’t forget that the outfit intended for baby bro was now crammed onto The Hunchback of Toddler Dame. Dad was all done problem solving by the time it came to my brother, who didn’t get any clothes that day. Instead, he was carried down the street in a diaper—and nothing else.

As she walked to meet us on the sidewalk, mom let this full picture of family chaos wash over her and decided to claim us anyway. We all went home together, and I’m sure my father did his best to shake off this ordeal and brace himself for the next one—because when you have little kids, there’s always a new ordeal right around the corner. But a lesson was learned that day: If fashion is just a gateway for self-expression, The Day the Toddlers Dressed Themselves offered my parents a glimpse of what life is like with children who are equal parts creative and strong-willed.

This article originally appeared in the September/October 2025 issue of (585).

Views: 5

Subscribe to our newsletter