Why I let my son wear shorts in the winter

It’s a blustery 35 degrees outside and we’re waiting at the school bus stop. All the kids are milling about bundled up in hats, gloves, boots, and big puffy jackets. But one child is doing something different.

That child is my son. He sticks out like a sore thumb because he’s wearing shorts and sneakers. No hat. No gloves. And underneath his hoodie is just a T-shirt.

I should explain how we got here.

My son has always been finicky about clothing. Among the things he doesn’t like are jeans, denim, zippers, buttons, wool, winter boots, “itchy” sweaters, clothes that are too loose, clothes that are too tight, and socks that go higher than his ankles.

Clothing also has to be put on in a certain way. Sleeves must be rolled perfectly to the wrist. Drawstrings for pants (because we don’t use zippers) have to be pulled just right, and tied with a square — not granny — knot (there’s a difference!).

My son’s ideal outfit consists of sneakers, track shorts with an elastic waistband, and a T-shirt. And that’s what he’d put on that windy winter morning. We’d been battling with him for weeks to put on warmer clothing. And it was making our mornings an absolute disaster. I was fed up with the arguing and drama. So I said to my son, “You know what? Wear what you want to wear.”

We headed out into the cold, and he walked ahead toward the bus stop in his shorts. I trudged right behind, carrying his winter jacket, gloves, hat, and a pair of pants. After a minute or two, he started shivering a bit. Another minute, and he casually asked for his gloves, which I gave him. As the bus pulled up, I stuffed his jacket, hat, and pants into his backpack. He got on and looked back. I could tell he was cold.

I’d love to say my son learned his lesson that day and started wearing pants to school. But that wouldn’t be true. He did, however, start to wear his hat and gloves more often. We’ve also tried using some of the tips experts suggest for getting kids to wear winter clothes, which has helped a bit.

And the other day, to my surprise, my son asked me what temperature it was outside. When I told him, he asked me if that meant it was cold. I said, “You bet it’s cold.” I could already see the gears in his head turning as he looked over at his winter gloves.

My son is going to wear what he wants to wear. But I’ll be sure to have his winter jacket nearby, for when he’s ready.