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What it Really Looks Like When My Kids Dress Themselves

08/06/2015 05:24 EDT | Updated 08/06/2016 05:59 EDT

Every now and then, I hear someone say, "Oh, I just love it when kids dress themselves. It's so adorable!"

When they say this, I know exactly what they are picturing -- a little girl wearing a fun combination of fashionable clothing, full of delightfully mismatched colours and unconventional pattern combinations, all topped off with a pair of sunglasses and an adorable floppy hat. So sweet!

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I see this sometimes on my Instagram feed, too. A photo of a comically cute and stylish toddler with the caption: "She dressed herself today!" And I think to myself, "Really? Is that what it looks like when your kids dress themselves? Because that is really not my experience."

That picture of my kid up there? I picked that outfit. I mean, she helped, which explains the striped tights, but I approved the tights and I insisted on the hat and the boots. In my experience, kids who actually dress themselves usually look more like this:

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That's my toddler in her favourite pajama shirt, and also her favourite shoes. She often wakes up in the morning, yanks off whatever she's been sleeping in, and then insists on changing into those PJ's. So she'll be "dressed," technically, but walking around in public in pajamas.

But what about when older kids dress themselves? My two older daughters received some really cute new dresses a few months ago, and they have a lot of good quality t-shirts and sweaters, all kinds of shorts and jeans and cords and leggings, and lots of adorable skirts and tights. Really, they have many great options, and I'm happy to help them decide what "matches" or what colours complement each other, if they ask. But whenever possible, my six-year-old selects this outfit here, even if she's already worn it twice that week. Because it's all blue!

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Or this one, which includes her very favourite shirt of all time:

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Before you criticize me for being too controlling and before you insist that she looks just fine, please notice that I took those pictures in public. I know she looks fine. She looks cute, even. But there is a stain and a hole in those blue tights, and that flowered t-shirt is supposed to be tunic-length and have long sleeves. She'd wear the same faded, too-small things every day, long after she's outgrown them, if we didn't have to wash them sometimes and if I didn't insist on handing them down to her younger sisters eventually. She looks fine, for sure, but my point is simply that if I were picking her clothes, she would have been wearing one of the many newer, nicer items that I only see when I open her drawer to put away her clean laundry.

Most days, however, I do my best to take a breath and let my kids wear whatever they want to. I try not to tell them that they'd look cuter, prettier, more stylish, or "better" in something else, unless there are obvious stains or holes I can point to in making my case. You see, fashion is arbitrary and I don't want my girls to worry about it much, if possible. I don't want them to care about how pretty they look. I want them to get dressed and then move on to the next portion of their day. If my daughter wants to dress as "blue girl," I'm not going to point out that teal and navy don't usually "match" very well. I want her to decide what she wants to wear and then simply wear it confidently, even to school.

I'm hoping that being able to have control over her own choices about the little things in her life now will give her the confidence to take control of the bigger things, later on. Also, I know there are many areas where I absolutely want and need to be in charge of her life -- what she wears should rarely be one of them.

Besides, there's a big bonus with this philosophy -- sending my kids upstairs to pick their own clothes in the morning is a lot less work for me than picking them out myself the night before. I'm always a fan of lazy silver linings.

But when you see my three-year-old wearing her favourite long-sleeved candy cane dress in August, feel free to laugh and say, "Oh it's so adorable when kids dress themselves!" Because sometimes, it totally is.

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Jacqueline believes that laughter and honesty make parenting easier for everyone, which is the goal of her blog, TwoFunMoms.com, where a version of this post first appeared.

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