It started when my daughter was three. She’s always been strong-willed and had a very distinct sense of style. Quickly we realized we could give her choices in what she wore to preschool each day.

At first, we’d let her choose between two different outfits. Now, she has free reign over her entire closet in the mornings before kindergarten.

Does that mean she went to school in early September in a tulle Halloween skirt and “Boo” sweatshirt? Yes. (The girl loves Halloween, okay?) But I have absolutely no regrets when it comes to our decision to let her dress herself for school, and here’s why:

1- Self-expression matters, and it brings your child joy.

Being able to express herself makes my 5-year-old daughter happy. Contagiously, belligerently, big happy. As a parent, it feels like we have to say “no” often–but if it isn’t hurting our child, or someone else, and if it doesn’t go against our values–why not say “yes” when we can? 

She wants to dress herself. She has a very clear and strong idea of what she wants to wear each day. When we started saying, “Yes!” it made getting ready for school infinitely easier.

And not only does it make her happy to have this autonomy over what she wears–it makes us happy to see her happy. It makes us excited to see what our five-year-old will come down wearing each day (because no matter how she dresses, we have learned it will definitely never be boring).

We want to foster independence in our daughter, and also her creativity, her own sense of style, and her own ways to access self-confidence. Self-expression in the things she wears gives her opportunities for that.

2-You learn life lessons best when you learn them for yourself.

This is the perfect opportunity to allow her to learn for herself why we don’t recommend a fluffy, heavy princess dress on PE day. 

Letting your child pick their own clothes is a low-stakes gateway to handling bigger responsibilities independently. 

And as a public school teacher for the last eleven years, one thing I learned for certain is that kids learn best when they learn it for themselves. When an adult tells them something, they may consider it or even do it out of respect or trust or duty, but once they’ve learned a lesson for themselves, it sticks. 

3-It’s always wise to pick your battles as a parent.

Some battles are worth fighting. For example–sticking to a bedtime routine is a non-negotiable for us. Keeping her bedtime is a battle I personally am willing to fight. I’m sure the worthwhile battles differ for each parent, but for us, letting our child choose her own clothes is not worth the fight. When your child gets to choose their own outfits, you know they will wear them. It not only makes life more fun for them–it makes life easier for you. 

This especially isn’t a battle I’m willing to fight when there are so many more benefits to letting her pick her own clothes than there are not to.

In fact, one of the only “negatives” is that it sometimes isn’t how I would dress her. But like so much of parenting, this isn’t about me; choosing her outfits is about her gaining her own sense of self. 

So bring on the Halloween-princess-mix-matched-fashion show every morning.