Like A Hero

Over the past couple of years, my son and I have been in a bit of a war about clothing – and it is a war that I have very slowly been losing, as the items that I pick out slowly get moved towards the back of his dresser, replaced by piles of gym shorts and t-shirts with pictures of pizza on them.

I would have better luck getting him to be nice to his sister for an entire week (IMAGINE?!?) than I would getting him to put a pair of jeans on his body. Collared shirts? Forget it. Anything that does not, to his mind, qualify as “soft” (which is a very specific term that does not include items that I myself consider soft, like a technically extremely soft shirt that also has a button located somewhere on it) is a no-go.

Now he’s going into kindergarten, which means he’s officially starting his journey through the insanity that is elementary school. I know from vast personal experience how tricky it can be to find your footing in this crazy new world where kids mock you for having the wrong backpack/friends/taste in food/hobbies/everything. I know how it feels to want to – and then fail to – fit in, so my plan is to teach him that nobody gets to tell him what’s cool except for himself. And one little way I can start is by letting him explore the idea of personal style – which may sound silly; superficial even…but I’ve always believed that when we get dressed in the morning we paint a picture of how we want others to see us, and, more importantly, paint a picture of how we see ourselves. That’s a decision that I think he should start making for himself.

If you go over to my Instagram, you’ll see the little surprise I put together for my soon-to-be kindergartener: I went to Sears, picked out a ton of on-sale pieces – focusing on stuff that I was pretty sure he’d like (the aforementioned soft items; anything with superheroes on it; absolutely ZERO denim or buttons) – and then piled it all into a backpack and left it on my bed for him to discover. (Sears offers a great selection of back-to-school items, so I was able to pick up everything he needs for the school year – from active wear and basics to backpacks.) When he came home, he got to go through everything, tell me what he liked and what he didn’t – he liked everything, YAY – and then pick out his outfit for the first day of school all by himself.

What he chose: A Superman tee and a pair of track pants (love them), plus sneakers that he placed on his feet and instantly declared “The most comfortable shoes I’ve ever worn!” (He really did say this, and I have literally never had the experience of buying him a new pair of shoes and having him do anything other than state that he’ll never wear them, ever, so perhaps these are…magic shoes? Who knows.)

sears back to school clothing for kids

I started out this post thinking this little exercise would make me feel…I don’t know, nostalgic, at the very least. Maybe even a bit sad. It’s not like he doesn’t already wear more or less what he wants to wear, but making it that definitive – “You’re in kindergarten now, and you get to pick your own clothes” – is a tiny little window into what’s to come. We’re going to watch him turn into a completely independent young man, with his own ideas about what’s right and what’s not for him. And I am nostalgic, thinking about that.

…But sad? Nope.

My son chose a Superman shirt to wear on his first day of school. Because he knows – just as I already did – that he’s going to take on this next step in his life like a hero.

If you’re looking for Back to School outfit inspiration (or need to shop for your kids’ own version of magic shoes and superhero wear), check out Sears’ Back to School catalog: it’s completely completely shoppable, and they have some great sales going on through August.

sears back to school clothing for kidssears back to school clothing for kids

This post was created in collaboration with Sears

  • Olivia

    Re-reading this and we may have the same child. Jeans are like a GIANT NO here.