I spent the first two years of my eldest daughter’s life wearing myself out, making sure her outfits were just perfect. I had a strict “no dress-ups outside of the house” rule, and only bought articles of clothing that I would want to wear myself. 

As soon as she could voice her opinion, my daughter made if very clear that she was not okay with wearing a black blouse underneath a tailored beige blazer. The old adage, “pick your battles” played on repeat in my mind and I conceded to letting my two-year old start dressing herself.

Six years later, I now have three young daughters and am a firm proponent of letting kids pick out their own outfits. I’ve found that there are multiple benefits (that is, once I got past the bizarre looks you get walking through Target with a child wearing fairy wings, two different kinds of rain boot, and an assortment of Mardi Gras beads tangled in her hair).

I’ve narrowed those benefits down to 4 key reasons why I continue to let my children dress themselves.

  1. Independence

The first step in letting my two-year old dress herself was to make her clothes more accessible. We bought her a little step stool and moved everything down to the very bottom shelves in her closet. She quickly learned which drawer held her pants, and how to unfold her socks in order to better maximize her chances of mismatching them. We were shocked by how capable she was of figuring it all out! This tiny little toddler who couldn’t even blow her nose could put together a complete outfit. And, not only could she put it together, she could also (sort of) put it on her body! MIND BLOWN. Does that mean that she always put her pants on the right body part? No…

But, come on, it’s just too adorable to correct.

Giving our children the feeling of freedom and independence is huge. We make most of the decisions in their young lives, from food choices to which friends they get to play with. It’s amazing to see the light in their eyes when they get to make a decision themselves.

  1. Confidence

It doesn’t take rocket science to know that people are more confident when they’re doing something they want to do instead of something somebody else is making them do. Just take for example any toddler whose mother naively puts milk in the wrong color cup. All hell breaks loose, right? It’s just human nature; we’re happier when we’re empowered to make our own choices. When my girls dress themselves, they’re proud of themselves and it shows. They rock the day; strutting around like they’re all that. And the really cool thing is, that confidence carries over to other things. Suddenly, they can climb those monkey bars, and they can get up in front of their class to share their show and tell item. So what if they can’t quite match an outfit…the things they can do far outweigh that vanity.

  1. Self-Expression

We all want our kids to grow up comfortable in their own skins, right? This point is really important to me; I want my daughters to continually explore who they are and what makes them happy. Why not let them start in on it now, when the most shady thing they can do is declare that they like Dora the Explorer (heaven help us all). When it’s time to go shopping for new clothes, I make it an all-day affair. I take them all with me and we weigh the pros and cons of each desired article. If they want something, they have to convince me that they will wear it all the time, and that it’s worth the money it costs.

Not convinced that your child can participate in a conversation about the monetary worth of something? You’d be surprised. In our house, we break money down into ice cream cones: “This shirt costs the same as three ice cream cones. Do you think it’s worth that?” More often than not, they’re the ones choosing against something because they feel it’s too expensive.

By taking my kids shopping with me, not only do I get an awesome experience watching how each of their own, unique styles evolves as they grow, but I also end up buying only the clothes that they will actually wear. We’ve all felt guilty about moving an unworn dress with the tags still on it from the dresser down to the basement. No more of that, I say!

Why yes, those are earmuffs doubling as a belt.

  1. Mama Freedom!!

This is perhaps the most rewarding point. I wake up in the morning, make a cup of tea, and sit down to enjoy the birds singing outside all while my daughters get themselves dressed for the day and come downstairs fully ready. Oops, one of them forgot their socks! No problem, she dashes back upstairs excited to pick out her mismatched pair. We eat breakfast together and then they put on their own shoes, coats, snow gear…whatever the weather calls for. Oh, and did I mention, they do it all on their own. Then, they confidently head out the door knowing that they’re going to rock the day in their striped pants and spotted shirt. And I smile smugly while still enjoying my tea, knowing I’ve got a great thing going.

Chelsea Flagg

Chelsea is a stay-at-home mama, comedic author, blogger, lover of goats, and a big fan of laughing at herself. When she's not online writing, you can bet she's hanging out with her three practically perfect daughters and charming husband in sunny Boulder, Colorado. Much to her chagrin, they do not own a cat. You can visit her at http://www.chelseaflagg.com/