PRETEEN FASHION: Let Us All Enjoy These Photos Of My Hilarious Fashion Mistakes

I’ve been noticing that kids aren't making any of the hilarious and memorable fashion mistakes that I made when I was their age. HOW DO THEY KNOW BETTER?
Publish date:
June 24, 2014
fashion, teenagers, embarassing pictures from my youth

There are few things I enjoy more than making fun of old childhood photos of myself. I realize that it’s generally frowned upon to laugh at children, but when you’re the child you’re laughing at, I think it’s okay. Let me get back to you on that. Anyway, there’s a middle school near my apartment in Toronto, so I see a lot of kids around every day (preteens especially), and I’ve been noticing that they’re not making any of the hilarious and memorable fashion mistakes that I made when I was their age. Why is that??? HOW DO THEY KNOW BETTER? Is it because of Instagram? Ugh, I bet they all follow Nicole Richie and know how to mix prints.

This recent disturbing realization led me to my mom’s house, where I pulled out old photo albums and took a stroll down memory lane, where I was quickly reminded of the weird crap I used to wear. I could not have been more all over the place with my “sense of style,” and while it’s unfortunate that those days were so well documented, it warms my heart to look at the photos now, throw my head back and laugh maniacally.

Before we start, I can think of no better soundtrack to guide us through this look back at preteen fashion in the ’90s:

Let’s begin, shall we?

HOLOGRAM (age 11)

Okay, this is a weird one because I KNOW it’s a ridiculous outfit, but I also know I kind of want a crop top and harem pants now. You should also know that the day this was taken, I was watching my little cousins get their photo taken with Santa at the mall. So to me, this outfit said, “I’m no longer one of the kids. I am a real-life grown-up…but I’m also festive.”

And wouldn’t you know it, it’s over a decade later and the hologram trend is back in full force. God bless the ’90s. Alyssa demonstrated three awesome ways to pull it off if my outfit isn’t inspiring enough for you. The key to making this look work for you in, you know, adulthood, is choosing one hologram piece and keeping the rest of your outfit muted and simple. Oh and, probably don’t choose ill-fitting pants as that one piece.


The actual outfit isn’t that note-worthy (paisley-printed top, maxi skirt with beaded flowers, blah blah) but THE SHOES. Those have to be at least three sizes too big on me in this picture. I didn’t notice them at first, but now I truly can’t see anything else. I actually have never gotten over my love of chunky boots, but my approach to them these days is…different. Lately, I’ve been obsessed with these cut-out ankle boots:

To be fair to 12-year-old me, I would still wear these with a skirt or dress these days. Sure, not a maxi skirt with a slit down each side, but STILL. I was on to something.


Lastly, and my personal favorite: my boho phase. This was the year I got a perm to match my newfound approach to fashion –- and life. This happened exactly how you think it happened: I watched "Almost Famous" for the first time, decided that the key to happiness was becoming Kate Hudson (I have yet to be convinced otherwise, btw) and I took off, grabbing every earth-toned, flowy piece that crossed my path.

The only real issue I encountered was that my cheerful closet soon no longer reflected my sullen, teenage angst-filled soul, so it didn’t last long, but it was fun for the short while that the universe and I were one and headbands of daises adorned my frizzy head.

These days, bohemian to me looks more like these beautiful prints, and less whatever that orange thing was:

From left to right:

Asos, $104; Tobi, $70 H&M, $10

What are your biggest fashion regrets from your preteen years?