Working Parent Parenting & Child Care by Stage Child Development Education Family Health Family Life In the News

Kids & Fashion: Allowing Children to be Themselves

Kids & Fashion: Allowing Children to be Themselves

Toward the middle of every summer for the past few years, I’ve started thinking about what my son (and now sons) will wear for the first day of school. I must admit I’m a sucker for the Pinterest-worthy first day of school pictures – kids with perfect hair, perfect clothing and the first day of school sign perfectly drawn on a mini chalkboard. I’ve never had a problem with getting Max to wear exactly what I wanted him to wear for the first day of school, a holiday or family gathering and getting that photo. Ben, on the other hand, HATES what he calls “party” or “wedding” clothes. Any shirt that has buttons, whether it be polo style or button down is deemed off limits by him and worth a fight for me. I’ve tried to instill that sometimes society requires that we just dress a bit nicer than our normal wear. Case in point, Kindergarten Prep graduation, when I told him it was a “rule of life” to dress up for graduations.

But this year was different. This year, after reading this blog post, specifically this, It’s also why you won’t see him dressed to the nines on the first day. He will wear what he wants so he feels “cool” in a whole new class. This is what I can do for him. It isn’t about me.” I totally changed my tune. She was right. The first day of school wasn’t about me. It was then and there that I decided to let the boys wear whatever they wanted on the first day of school.

Brothers on First Day of School

I know how it feels to have the perfect outfit for a situation. That outfit that’s comfortable and exactly what you wanted for that exact situation. I know how confident it makes you feel and I wanted nothing more for Ben on the first day of Kindergarten. He ended up choosing an outfit he’d worn 1,000 times that summer but with his shiny new sneakers and he was so happy.

Today was picture day and I followed the same thought process…for the most part. I was able to gently guide him toward a casual polo shirt versus his favorite Batman t-shirt, but it wasn’t much of a struggle and he happily got dressed this morning. There were no new pants or fancy shoes to be found and if we’re being completely honest, I didn’t want him to wear a t-shirt because I didn’t want his teacher or the other parents looking at the class photo to think I had forgotten picture day. If he had asked to though, I would have let him.

Kindergarten Boy on Picture Day

His brother on the other hand, my little hipster fashionista, insisted on wearing a tie. And even though I’d already ironed another shirt, which I hate doing by the way, I let him rock what he loved too.

2nd Grade Boy on Picture Day



  1. Brandy September 29, 2014 at 8:02 am

    Thanks for the shout out! They are adorable!

  2. Media Mom September 29, 2014 at 9:36 am

    These might possibly be the cutest kids in the cutest outfits I have ever seen — that includes the first day outfits and picture day! And I feel your pain too. Ironically, my 2nd grade girl will let me pick out her clothes 95% of the time. My preschool son however, refuses to wear a shirt with any kind of button, zipper etc. Luckily for us, the one wedding he’s been too was about 2 months before this “phase” started. Now its been a year and a half, and he hasn’t budged an inch. He also hates the change from pants to shorts in the summer and the change back to pants in the fall. New shoes are a struggle, but only for the first day. Picture day is coming up for us, and I’m on the hunt for some nice crisp t-shirts. I don’t care what he wears for his own photos, but I don’t want the other parents feeling like he’s the slob in the class picture. 🙂

  3. CuteRascals December 11, 2018 at 2:20 am

    I completely believe that kids should be allowed to dress the way they want and there should be no unnecessary interference from parents side.But in this case a proper idea and advices are also needed as to what should these kids wear to look and feel simple.I usually prefer visiting cuterascals as they have a lot of variety and more ideas can be gained as to what should be purchased.

Please Log In to Comment