What it really means to let your kids dress themselves

By Jac

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 mis-matched colours and unconventional pattern combinations, all topped off with a pair of sunglasses and an adorable floppy hat. So sweet!

Maybe something like this photo of E:


Animal print, stripes, cute boots, and adorable hat? Check! Aw, she dressed herself today!

I see this sometimes on my Instagram feed, too: the caption, “She dressed herself today!” with a photo of a comically cute and stylish toddler. 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 E 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 dress and the boots. In my experience, kids who actually dress themselves usually look more like this:


That’s R in her favourite pyjama 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 pyjamas. See:


Also, there is the backpack. Everywhere we go, she needs to take that backpack, and it has to have her favourite Minion stuffie in it. That’s generally what it looks like when my toddler dresses herself, and that’s on a good day. I remember one time this summer when I decided to let her pick her own clothes and she tried to convince me she should wear two flannel sweaters and nothing else. In August. And so instead we work together (ie: lots of fighting), and try to come to some kind of a compromise. Sometimes I just pick her clothes and shove them on her, and then quickly distract her with tickles or snack time so she doesn’t notice she’s dressed.

What about when older kids dress themselves, though? My two older daughters received some beautiful new sweater dresses for Christmas, and they have a lot of good quality t-shirts or sweaters, all kinds of 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!


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


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 put away her clean laundry. Or something more like this:


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, or prettier, or more stylish, or “better” in something else, unless there are 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 G wants to dress as “blue girl,” I’m not going to point out that teal and navy actually don’t 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 want and need to be in charge of her life; what she wears does not usually need to 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.

R also got a new dress for Christmas. At first she didn’t want to put it on, but I made an exception to my usual philosophy and forced her flailing and raging limbs into it because, you know, Christmas. By the end of the day, however, she screamed and cried when I took it off, and then she asked for it again the next morning, immediately after she woke up. She also likes to accessorize it with a plastic tiara. It is definitely January now, and she still wants to wear it every day.


So when you see me in the Spring and my daughter is dressed like a candy-cane, feel free to laugh to yourself, and say, “Oh, I just love it when kids dress themselves! It’s so adorable!” Because sometimes it totally is. 

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