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I Let My Toddler Dress Me for a Week — Here’s What Happened

I have picked out my son’s outfits almost every day of his three years on this planet. I thought it would be fun to turn the tables and let him pick my outfits out for a few days. How crazy could it be? I like everything in my closet, and I mix and match items all the time. Well, let’s just say it was interesting. And above just being interesting, it was a fun experience to have with my little guy. I also learned a few things from my pint-sized fashionista. Check out Rockwell’s awesome fashion sense below …

Day 1:


The first few items were great: my Bob Dylan tee, with a gray skirt, and tights. I think I’ll put this in my rotation. Fabulous choices, Rock.

But then before I could finish, he pointed to my nude heels.

“Are you sure you want to pair these tights with these shoes?” I leadingly asked.

“Yup,” he added without hesitation. “And the blue sweatshirt.”

I walked down the stairs to show off my outfit to my husband. I waited for a laugh, but he didn’t notice anything different. I decided his lack of reaction was either the fact that I’m constantly wearing things that are a little out of the ordinary, or that I’d trained him too well. I didn’t press him, figuring, “You look great in everything,” would probably be coming next.

Day 2:


This was probably my favorite day. These polka dotted Lula Roe leggings look great with my Mickey T-shirt. And although I wouldn’t have worn it with these shoes, it does have a fun feel to it. It’s almost like an homage to Minnie.

Day 3:


It started with the socks.

“I like flowers,” he explained to me as he pointed to my new Woven Pear socks. The dress choice made sense too, as he pointed out matter-of-factly, “They both have flowers.”

His excitement for picking out the shoes was through the roof. “These!” he cried.

I smiled at him and put all three pieces on. “Should I put a sweater on?” I yelled to him.

“Or how about this jacket?” he timidly asked.

“That would be perfect,” I gushed. It was so much fun to see his face when I followed through with what he suggested.

(Side note: I was a little self-conscious running my errands that day, but again, to my surprise I didn’t get one double-take or stare of curiosity. Instead, I got a woman who stopped me to tell me she liked my socks!)

Day 4:


This outfit was a little more of a challenge. He picked out three shirts for me … and that’s it.

“Mommy can’t go outside without any pants on,” I explained to my 3-year-old. “How about we switch one of these shirts for a pair of pants?”

He nodded his head in understanding and pointed to the closest pair of pants. He also pulled out two pairs of shoes from a pile in my closet. I don’t think he realized that they were two different shoes. If my closet was at all organized, he probably wouldn’t have had that problem.

Day 5:


This shirt was picked out because it has arrows on it, and Rockwell loves arrows. He looked for pants that also have arrows, but had to settle on a pair of jeans.

“I guess you have to look for some pants that have arrows on them,” he seriously informed me.

I guess I do.

He also pulled out two boots, a rain boot and a brown cropped boot. He looked at them and asked, “Are these close enough?”

“Yup they are,” I replied.

I could tell that he was glad this was the last day. His busy toddler schedule is packed with a lot of fun things and picking out my outfit every day was starting to take too much out of his day. When it came down to it, he’d rather be painting or riding his bike.

So what did I learn from this experience? A lot of being a mom is telling people what to do, and it was therapeutic for both of us to change roles, if even in this small way. He enjoyed having his opinions heard, but he was also done after a certain point. I would recommend letting your little one pick your outfit one day this week and seeing how it goes. Not only will it be something that they remember, it was also be liberating. I realized how little people really care about what you’re wearing. The pressure we put on ourselves to look a certain way is just that: pressure we put on ourselves. I wore two different shoes for two days, and no one noticed until I pointed it out. You can be playful with your clothes, or casual or stylish, but it’s really up to you. The last thing I learned from this experiment, is to find moments to be silly. Silliness is good for your kids and for your heart. Don’t take yourself to serious: they’re just clothes.


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