Why I Let My Preschooler Choose His Own Clothes

I was six-weeks-pregnant when I bought my son his first piece of clothing: A MAFRAT Made In Italy denim jacket. The size? Zero months—not even 0-3 months. It wasn’t over $100, but it wasn’t under $50. I peg this absurd purchase to hormones.

The soft denim jacket had perfect white and red stitching, silver buttons with the designer’s name carved in them and a cool loop design on both front pockets. It was the first of many adorable pieces of clothing, accessories and shoes I bought my son, Jack, who is now six and a total spitfire with a talent for getting grass stains on his clothes.

I loved dressing him up for no reason. Button-down shirts, corduroys, and tiny Converse just to go for a stroll around the neighborhood. Slipping bite-size checkered Vans on his chubby baby feet for an afternoon in his swing. Color-coordinating our outfits was fu—I loved when people noticed my pink sundress and Jack’s preppy pink polo.

I got a solid, four glorious years of dressing my blond boy—but then something happened.

“Mooooooo-om,” Jack said on our ride home from his former daycare. “Alex wears comfy pants everyday to school!”

I quickly eyed up my kid in the rearview mirror. He had on dark wash jeans and a striped rugby shirt.

“Well, you wear comfy pants on Fridays,” I said. And by that I meant, a matching Adidas tracksuit or a cute sweat set from Old Navy.

Since Jack was 4 back then, the conversation quickly changed to wanting a hot dog for dinner. The next morning I set out camo cargo pants and a long-sleeved T-shirt with a pair of neon sunglasses on it. This will look awesome with his lime green and grey Nikes, I thought as I picked through a wicker basket that held his sneakers.

“I’m NOT wearing those weird clothes!” Jack insisted. I ignored him and pulled his PJ top over his head. It was a struggle. He called me “Mean Mom.” A sneaker got thrown at the wall. Jack got a timeout while I brushed my teeth, but we both left dressed—Jack in the outfit I chose and me in a black mini sheath dress with a square neckline.

When I picked Jack up that day and asked his teacher how his day was, she told me Jack needed to start picking out his own clothes. It was a little off-putting. I couldn’t believe his teacher was telling me how to … parent. But, then she went on to tell me that picking out clothes is part of being independent, yadda-yadda. I looked around the classroom. There were little girls in leopard ballet flats, polka dot socks, leggings dotted with daisies and embellished tops. They didn’t match, but kind of looked like little Carrie Bradshaws. The boys were all in comfy pants with elastic waistbands and t-shirts with cartoons splashed on the front—and there was my little hipster in his cool sunglasses shirt I bought online.

The next morning I let Jack pick out his clothes. He chose baggy, cotton elastic waist pants (that he wears around the house), a ninja T-shirt, hoodie that said “Santa Monica, CA” and dress socks. Cringing, I allowed him to dress and pick out his sneakers. He chose a pair with Velcro closures and told me he didn’t need help. I praised him for his independence and secretly, for possibly starting a new trend among the preschool set: Dress socks and sneakers.

We had entered a new era now and there was no turning back. Jack was now dressing himself and to assist him, I purchased new comfy pants and slipped them into his drawer. I stopped worrying so much about his clothes. My new motto: If they fit and they’re clean, you can wear em!

But then it was picture day at school and I had to throw down like Anna Wintour. It was a bad morning. All hell broke loose!

I laid out new, adorable skinny cargo pants in an olive green, a soft tee in grey and a white-grey-green button-front shirt. Jack threw them in the air and I watched them float across the room in slow motion. “I’m not wearing those wobbly, crunchy pants ever!”

I chased Jack around our condo begging him to get dressed, threatening to give all his comfy pants away to a little boy named Timmy who had NO clothes, to finally dressing him from top to laced up black Converse high tops bottom. He looked awesome even though he insisted the tags felt like “crickers” on his skin, the buttons on his shirt were “babyish” and the pants were also “sticking” to his knees. I was internally delighting in the fashion vocabulary my child was inventing: Wobbly, crunchy, crickers, babyish, knee-sticking! Who needs peplum hem, pencil skirt and bootcut!

A month later his smiley school pictures arrived. You never would have thought a post picture day breakdown had ensued just hours before.

Parenting is a huge undertaking, so checking fashion off my list of worries doesn’t seem so bad. Life pressed on. After a particularly long day, as we walked to the garage-level elevator bank of our building, Jack noticed I was wearing flip-flops and carrying a pair of snakeskin 4-inch heels.

“Why are you wearing flip flops mommy?” Jack asked.

“Mommy doesn’t feel like wearing her fancy shoes right now. My feet hurt,” I said.

“Yeah, I don’t like my crunchy pants today, too!” he said.


When we got upstairs we both changed into our jammies, cuddled on the couch, and ordered a pizza.