About three months ago, I gave up. I gave up on the morning duels with my 3-year-old over what he was going to wear. I would pick out his clothes for the day, he would throw a tantrum and the morning would turn into one large hot mess before we even tried to get in the car.

One day, I got to my office and put my head in my hands. The mornings were absolutely exhausting because of the battle with Henry over his clothes.

Then I realized I should just let him pick out his own clothes. No, he would not wear the cute polo shirts and skinny jeans that I wanted him to wear, but he would be happy and my mornings would be a million times easier.

So the next morning, I told him to pick out his outfit. He did, got dressed, we headed to the car, I dropped him off at preschool, and went to work. No tantrums, no yelling, no negotiating with a 37 pound hostage. It was magical.

From that day on, Henry has been picking out his clothes. At first, I was absolutely embarrassed by the fact that he wanted to wear the same Batman shirt with gray sweatpants, rain boots and a rain jacket every day.

But it kept the tantrums away and he is his own little person. I decided I shouldn’t force him to wear clothes that he didn’t like. They were probably uncomfortable anyway. If I could, I would wear a t-shirt and sweatpants every day too.

When I realized that the Batman shirt wasn’t a phase, I went and bought him three more Batman t-shirts. He rotates those with various sweatpants, rain boots and a green rain coat. Every. Single. Day.

When Easter service rolled around, I let him wear his Batman shirt, boots and rain coat. I did make him wear gray slacks instead of sweatpants. So that was a small win.

And when I found out that his preschool was having picture day, I just knew that he would be wearing his signature look. And I could not care less. Because I wanted the picture to be true to Henry.

And boy – was it ever.

I opened my email the other day and saw this amazing photo.

I literally laughed so hard I cried. It was horrible. But it was amazing.

Everything about this picture explains my little boy. And I love it.

He is mischievous, messy and constantly on the go. He is so sweet but can also be so bad. But he does everything with purpose. And he knows what he wants.

So I spent $48 earlier buying copies of this photo. Because it is everything I want to remember about my oldest baby.

And I can’t wait to put a copy of it on my desk so I can laugh each and every day when I look at it.

Because it is so bad, it’s beautiful.

And if I had made him wear a polo and a pair of khaki pants, I wouldn’t have the chance to remember his headstrong personality at such a young age. When I am sure he will be a headstrong adult.

So I am going to continue letting Henry pick his own clothes out every morning. And hope that I continue getting more photos like this.

Until Next Time,

Jamie

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