How do kids feel about their clothing style at school?

If there’s one piece of parenting advice that I’ve heard over and over again, it’s “pick your battles.”  But what if I’m not looking to battle, but to find a middle ground? Do I have to give in all together? One area where I find this happening – and please don’t stop reading when I say this—is with what my kids wear.


Yes, I know that it’s silly and who really cares, but they are still at a cute age where I get that warm and fuzzy feeling when they’re in something that I really love. Add me to the “you’re a bad parent list,” but I know that others feel the same way even if they won’t admit to it. I will say that I’m not willing to have a fight over what they wear, especially now, but I do want to try and steer them in a direction where we are all happy. After all, we all express who we are through what we wear and that’s important for self-esteem, as I learned from talking to a few experts in childhood education.

 After my friends gave me a hard time about having major opinions about what my kids put on, I decided to call around and get some expert advice. I wanted to know if my pushing qualified as somewhat annoying or truly bad parenting. My first call was to Richard Peterson, Chief Academic Officer, at the Kiddie Academy. He told me that “at a younger age, children discover newfound freedom by selecting the clothes they are going to wear each day and dressing themselves. As they get older, picking out their own st‌yle of clothing instills creativity. Children build their identity by how they look and what they wear, which is an important part of adolescence; they are discovering new freedom which they didn’t have in the past.”  After our conversation, I felt that this was a valid point. Children learn important life skills by exploring and making decisions, and even the youngest children should have this opportunity.


But still, I wasn’t fully convinced to change my ways just yet.


So I sent an email to Elyssa Katz Founder and CEO of The Zutor Concierge. Mom-to-mom she told me “I was the parent that loved to ‘dress-up’ my boys from an early age. I had many rules such as no graphics, no logos, no superheroes. As my children have grown up, I realized that controlling their st‌yle is not beneficial for any of us. It causes unnecessary stress for everyone because in the end does it really matter if my child wants to wear a Superman shirt to school? Now I realize that allowing my children to dress how they would like empowers them and makes them feel successful starting from the time they wake up.” This comment really hit home for me and while I felt better that someone else had gone down the same path, clearly my outcome also needs to be a positive one. Does my enjoyment of what my kids wear outweigh their overall happiness and our family’s stress levels which are already high? I’m starting to think not.


My friend Sarah Tropeano mentioned that a curated subscription box might be something fun to try and a good way to balance what I like with allowing my kids the freedom to choose what they want to wear. It could be the best of both worlds! So, I tried kidpik which has boys and girls head-to-toe mix-and-match outfits. Because kids fill out a quiz, they get what they like. In a few days, a package arrived with items that both my kids and I loved. The whole experience was completely risk-free and the price is reasonable.


On my quest to get as many opinions as possible before making my final decision, I asked mom and CMO of kidpik, Dina Sweeney what her advice was. “We’re in a new school year filled with uncertainty, but one thing is certain, feeling good in your clothes is important for building confidence. The power of an outfit that allows you to express yourself is transformative. For school at home, cool and comfy matching lounge sets or elevated activewear is a great choice over keeping on PJs. Putting on a ‘real’ outfit helps kids in the mindset of school and creates structure.”


That’s when I decided to throw in the towel and accept that what I was doing was not constructive. My nitpicking was causing unnecessary disagreements, increasing everyone’s stress levels, undermining their self-confidence, and hindering valuable life lessons. Plus, I discovered that subscription boxes are a fun and timesaving alternative – bonus!


Giving Kids a Voice


One of the most important emails I received in my quest came from Elaine Taylor-Klaus, PCC, CPCC, CEO, She told me that “if a child is not expected to wear a uniform, then giving them a voice in what they wear is essential to helping them foster self-determination and cultivate problem-solving skills. Kids tend to feel controlled in many aspects of their lives (“do your homework, take out the trash, etc.), so giving them choice in an innocuous way can empower them to feel capable and avoid the inevitable push-backs that come when they start to feel too controlled.” That sealed it for me. As long as the kids were dressed and happy, so too would I be.


School is about learning and this back to school I learned about standing back for a moment and paying attention to what’s really important. What seems like a silly desire, wanting my kids to look cute at every moment, is actually taking away valuable lessons from them. I’m looking forward to calmer mornings and happier kids. I should have made this decision a long time ago. But like they say, “Live and learn!”

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