My Kids Are Harder To Dress Than Yours

Day 1 of Parenthood: Reality Poops on My Dreams

When I was pregnant with my first child, I allowed myself to buy one baby girl outfit even though I didn’t know what I was having. My motherly intuition told me it was a girl, and like many a first time mom, I had dreams of dressing her up in ruffled dresses, sparkly tutus and ballerina slippers. To tide myself over, I bought a cute but inexpensive watermelon patterned outfit at Costco with the plan to return it if I had a boy.

When my daughter was born, I could not wait to try it on her! In my postpartum, barely-functioning, anemic stupor after a rough birth, I managed to hobble out of bed and dig the watermelon number out of my suitcase. I realized right away that it was a bit snug—she weighed 9 lb 6 oz at birth and had apparently skipped right over newborn sizes. Undeterred, I put the outfit on her for a quick photo shoot. Within minutes, she unleashed a spectacular meconium blowout that went all the way up her back to her shoulder blades, ruining the outfit and with it, my fantasy of having clean, well-dressed children.

It was an early clue that my kids would have absolutely zero interest in looking the way I wanted them to. In fact, over the years, they’ve continued to—sometimes literally but usually metaphorically—“poop on” my ideas for how to look clean, presentable, and appropriate.

My Kids Are Adorable Too…But in a Scrappy, Feral Sort of Way

You may be wondering why I’m choosing to bring this up. The truth is, I was recently triggered by a post from another mom. I’m not going to tag—I am not trying to start something and I’m sure this person is lovely, and a good mom. I am also sure that her kids are more compliant, more cleanly, and a lot easier to dress than mine! Anyway, here was the note:

Dress your children in clothing becoming their dignity. We can do better than little girls in graphic t shirts, leggings and crocs. We can do SO much better. Boys can do better than slumpy hoodies, joggers and slide shoes. Have we progressed throughout human civilization to end up in clothes that peasants 100 years ago wouldn’t be caught dead wearing?

Whenever I get triggered by something a stranger posts online, I try to pause and reflect on what it says about me. In this case, it was embarrassingly obvious: I felt defensive because I desperately wanted to have proper, clean, well-dressed children—the kind you parade around in public so people think, “Wow, that mom really has it all together!” But that was never my reality. I got the kids who wear hoodies to church, Crocs during cross country races (he is quick to point out that he got a personal best), and who simply won’t be forced into dresses, collared shirts, dress pants or even jeans!

Don’t get me wrong—my kids are adorable—in the way that babies with birthday-cake frosting smeared all over their faces at their first birthdays are adorable. It’s just that when you reach the tween years and still have food on your face, refuse to wear shoes around the neighborhood, and consider sweatpants an acceptable choice for 8th grade graduation, people tend to find it…less charming. Incredibly, sometimes those people even blame your mother! They make off-handed comments to her assuming she is the one responsible for the poor clothing choice. This is unfair.

Before we had kids, my husband and I once had dinner in a sushi restaurant. Sitting nearby was a 3- or 4-year-old boy in a sweater vest, eating with chopsticks (and no—he wasn’t Asian!) and charming every adult at the table. We looked at each other and said, “We can totally do this parenting thing. Why does everyone make it sound so hard?”

Fast forward 17 years, countless embarrassing exits from restaurants after colossal spills, tantrums, and tips as big as our meal to make up for the mess, and we realized we would never take our kids to a place like that—partly because they refuse to dress or act the part. So on a recent anniversary, we went to a fancy restaurant by ourselves thinking “it will be nice to do this without the kids.” Behind us sat a picture-perfect family of four: dressed to the nines with little girls in dresses and tights, napkins in their laps, eating food our kids would have scoffed at. These children sat patiently through multiple courses over hours.

So apparently these neat, clean, appropriately dressed kids do exist. I’ve seen them out in the wild, and I even know some of them in real life, like the family friend whose daughter asked me for a napkin when she got a smidgen of food on her fingers at my son’s birthday party. I was shocked, being so used to my kids simply wiping their dirty hands on the walls or furniture to clean them off. While I am not sure whose kids are more “normal”—my friend’s kid or mine—the difference is night and day. And there’s no question whose kids are harder: MINE.

A Brief Tour of My Kids Hating Shoes, Socks, Baths, Showers, Winter Clothing and Hair Cuts

My kids are 16, 13 and 10…so I’m happy to report we’ve outgrown a lot of the most embarrassing phases.

First, there was the “won’t wear shoes” phase which generated a lot of comments from worried neighbors and grandparents. Then there was the sock-refusal era, the phase where my son’s insistence on putting his naked feet in winter boots led to shoes so stinky we eventually got an embarrassing letter home from the teacher.

There was the bath/shower resistance phase wherein my kids felt that being asked to bathe or shower was akin to torture. With appropriate bribes, we could get them to wash themselves maybe every 2-3 days if we were lucky, and we started to count dips in the pool as “bathing” because it just made our lives easier. Thankfully this phase ended before the B.O. of teenagerhood set in, but it still wasn’t always pleasant!

There was the general refusal to dress appropriately for the weather phase—which I’m sorry to say has NOT yet ended. When they were little, I tried the “Love and Logic” approach of giving them choices. “You can wear your coat or carry it. Which do you choose?” Unfortunately my kids were too smart for that. They chose option C,—leave your expensive winter coat behind in an unknown location where it can never be found again.

Even today, my kids are pretty convinced that a hoodie can substitute for a winter coat, even if there’s a -10 degree windchill. This phase prompted me to post on Facebook in self defense “Note to our friends and family: I have purchased winter coats, boots, mittens and hats—my kids are simply choosing not to wear them. Please address any comments about being inappropriately dressed for the weather to them.” We live in Wisconsin and I actually view it as a miracle that none of my children has ever had frostbite. I guess there is at least a little truth to the basic self-preservation argument—kids will usually put on appropriate clothing or go inside before sustaining serious injury.

All three of my kids have gone through a “hates haircuts” phase. This was manageable with my daughter, but it’s more of an issue with the boys. I don’t mind long hair on boys, but mine tend to look like Wookies if they go too long without a trim.

When my middle child was about 9, I bribed him with a pet betta fish to get a haircut. That turned out to be a terrible idea, because suddenly a precedent had been set: now any kid in our family who sat for a haircut thought he or she deserved a new pet. You can imagine how well that played out.

The next haircut didn’t happen for another six months, as my kids held out for the possibility of a hamster or a bunny. And unfortunately, the haircut-refusal phase is still alive and well in my current 10-year-old, who would rather wander around looking like he has a mop on his head than endure 20 minutes in the chair at Sport Clips.

Are Your Kids Photogenic? Lucky You!

My kids aren’t just camera shy—they’re camera avoidant. I get it—in a world of smartphones, childhood basically feels like one long, unsolicited photo shoot. I find it annoying too. But still… it would be nice if, maybe once a year, they’d smile and look at the camera.

And as part of their general “we don’t care what we look like” philosophy, they definitely don’t care about looking good in pictures. After combing through every photo from 2025 in a desperate attempt to create a Christmas card, I did not find a single image where all three looked remotely presentable. I finally settled on a shot where the two older ones are flanking their little brother, who is in a full-on headlock and essentially being choked. They look happy and goofy—and honestly, it was the most accurate depiction of my children I could find all year.

A few weeks ago, I spent time with my niece and nephew, who are the exact opposite. My niece loves dressing up and always looks adorable. Multiple times a day she’d chirp, “Tía, take a picture of me!” I got more adorable photos of her in 24 hours than I’ve managed to get of my own kids in twelve months.

So yes, I know those picture-perfect, photogenic children exist. They’re just not in my immediate family. Good for them! No shade. I hope I get a copy of their adorable family Christmas card!

The Myth of Parental Control

By this point in my sob story, you may be thinking “Well, you’re the parent. Can’t you just make them wear what you want? Get the haircut? Pose for the picture? Engender obedience. Show them who’s boss! Draw your line in the sand.”

To this I would respond…respectfully, you do not know my kids. Maybe your kids allow you to dress them in whatever you want. Maybe if they’re older they even go and change with minimal complaining when you ask them to put on something more appropriate. In short—they’re easier than mine. My kids’ strong personalities dominate, so I need to pick my battles. And for many reasons—clothing choice is not it!

Let’s talk about the time I bought my son an adorable penguin sweater for $40 dollars to church on Christmas Eve, only to have him throw an hour long tantrum because the collar was too itchy. Eventually I gave in and he wore a sweatshirt. We were so late to church that we couldn’t get a seat, and it turns out the cow costume he wore in the Christmas pageant covered up what he was wearing anyway. Goodwill got a really nice donation after that, and I learned an important lesson—do NOT waste money on dress clothes that my kids will never wear.

You could say that, when it comes to clothing choice, I live by the “Let the Wookiee win” philosophy. Based on my research (I am not really a Star Wars person) it comes from a scene where Chewbacca (the Wookiee) is playing a holographic board game called Dejarik. When he starts getting frustrated, Han Solo warns C-3PO that Wookiees are known to pull people’s arms out of their sockets when they lose—so it’s smarter to just let him win. This is kind of how I felt about my little munchkins. Why provoke them and cause trouble over something as insignificant as clothing choice?

Final thoughts

If your kids love to dress nicely, have an innate fashion sense, or are simply cooperative when you try to make them look presentable—wonderful! You are genuinely lucky, and I’m happy for you. I bet your family Christmas card is adorable. Nothing I’ve said here is meant as an attack on you or your beautifully dressed children.

If I’m being totally honest, my kids probably inherited at least part of their laissez-faire attitude about personal appearance from me. Shoes—especially ones with laces—are annoying and, come to think of it, I ran around my neighborhood barefoot until at least ten or eleven. And I’m pretty sure there’s a study somewhere claiming it’s better for your posture to go barefoot anyway. I’ve never been the type to spend a lot of money on clothes, shoes or make-up (at least until I discovered Boden—check them out!) Also, why do we take so many photos? It’s ridiculous. How many perfectly good family moments have been derailed by the smartphone paparazzi? Leave these poor kids alone!

But yes, the situation I’ve described—kids who genuinely do not care what they look like—is not always ideal, but it’s what I’m working with. I just ask for a little grace when I choose to pick my battles, and this particular battle is just frankly not that important to me.