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.)
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.
This post was created in collaboration with Sears.