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My 62-Year-Old Mother Dressed My Tween Daughter for a Week and It Was … Interesting

My daughter is on the cusp of becoming a teenager. She sometimes chooses outfits I would not pick for her — but I’ve always let her do her thing when it comes to getting dressed. Not only is it one less thing I have to worry about, but it’s not my body. My daughter knows what she likes, what she feels good in — and I clearly remember being her age, when it felt like what I wore was everything.

These days, my daughter loves to dress in the latest trends, which seems to include lots of snug fitting clothes, high-waisted jeans and shorts, and sporty outfits, like athletic pants and a crop top or tank. Whenever I try to convince her to get something that has a bit more give, I can see in her face that she’s uncomfortable and just doesn’t love how she feels.

Still, when I said I thought it would be a fun experiment to have my 62-year-old mother dressed my 12-year-old daughter — and they agreed! — I was excited to take a step back and see how this would pan out.

You see, my mother shops at Sears, and still talks about the Montgomery Ward catalogue like it is a long-lost friend. She’s very conservative — while my daughter is super edgy. And neither one is even a smidge like the other when it comes to picking out clothes.

What could go wrong?

Day 1

girl sitting in chair
Image Source: Katie Smith

While my daughter likes these two pieces and wears them quite a bit, I was surprised she did not like this outfit.

“I would just never wear these together. I would wear the top with shorter shorts because the top is big and flowy,” she said.

It’s all about proportions. I loved this on her, of course, and I would have picked it out for her myself. Heck, I would even wear it. But for my Anna, it was a no-go.

Day 2

girl in black dress
Image Source: Katie Smith

This black dress is adorable, and I remember the day she saw it and had to have it.

“I loved this outfit, I wouldn’t change it,” she said.

She wears it all the time with sneakers or sandals. Good job, Grandma.

Day 3

girl in cap
Image Source: Katie Smith

Again, I was shocked my daughter didn’t like this ensemble.

Said Anna, “I would never wear jeggings with a sporty top, and the hat just doesn’t go with it at all.”

Now, in my mother’s defense, I don’t think she knows what jeggings are. They look just like regular jeans, so of course they would go with a sporty top? But according to my Anna, sporty tops are a no-no with leggings. Who knew?

Day 4

girl in chair
Image Source: Katie Smith

This was my absolute favorite outfit out of all my mother’s picks. But Anna said she picked out the kimono top to wear with crop tops and shorts, or over her bathing suit — not to wear with jeans and a full-length shirt.

I am wondering if it will fit me? I even have the white jeans to pair with it.

Day 5

girl in dress
Image Source: Katie Smith

I knew my mom would be drawn to this dress; it reminds of the dresses she used to buy for my sisters and me when we were younger (from Sears, of course).

I thought maybe my daughter would have outgrown it, since we bought it out a over a year ago. Instead, said she still loves it but wouldn’t wear it unless she had to get dressed up for something. She used to want to wear pretty little dresses like this every day, but alas, she has passed through that stage.

Day 6

girl in gray jumpsuit
Image Source: Katie Smith

Super cute and comfy, this is one of Anna’s favorites — so she was more than happy to wear it for the day, although she said, “Grams got the accessories all wrong. I would wear different ones. Like a choker would look way better.”

Day 7

mother and daughter
Image Source: Katie Smith

I think my Anna was more than ready to take over her wardrobe again and let her own style come through, so I decided since she was such a good sport, she could put her own outfit together. And so she did — on a shopping trip with me, of course.

Honestly, if my mother had wanted to dress me for a whole week, I would have said, “No way, someone please help me.” Not because I think she has bad taste. It is just very different than mine. Or so I thought. Turns out, when it comes to what my daughter wears, we both share the same sentiment.

Still, we learned very quickly that Anna has a system for what she wears, and she is very specific.

We can teach our kids they are just “clothes” and it shouldn’t matter, but I know better. It matters. As a longtime lover of fashion, I believe it’s a form of self-expression and deliciously fun. We all want to love the way we look. So while this experiment was interesting, I can tell the difference in Anna when she wears something that makes her feel like her best self.

And there is nothing wrong with that.

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