POPSUGAR Celebrity

Surprising Things You Learn Looking Back at Old Grade-School Pictures

Sep 2 2014 - 5:30am

I was back home a few weeks ago, and with my Facebook feed overrun with back-to-school pictures [1] (not just adorable #TBTs of former classmates, but current pictures of their kids), it got me feeling pretty sentimental. I rummaged through boxes of childhood photos and came across more than a few school pictures that, while embarrassing on many levels, got me thinking things like, "Man, I worked that puffy-paint sweatshirt." Or, "Dang, those plastic pumpkin earrings were the perfect accessory for our first-grade Halloween [2] party!" Or, "Who wouldn't want to wear a backward neon bucket hat to recess?!"

So, I nudged a few more of my fellow POPSUGAR editors to dig up their old school photos and share the style secrets they knew even way back when. Here are a handful of things we learned by waxing a little '90s nostalgia. (Rule No. 1? When in doubt, carry a slinky.)

You Worked an Oversize Handbag

"I'm pretty sure my mom chose this pastel outfit for my first day. And what was she thinking with that lunch box? It's huge! If it was up to me, I would have matched my older sister from head to toe. I always tried to copy her style growing up, which is funny because now she's the one who borrows my clothes!"

Stephanie Wong, editorial development assistant

You Layered With Abandon

"I have a very vivid memory of picking out this outfit. The sweatshirt was Esprit, and it had a design on the back. I remember thinking that, although the magenta shirt underneath didn't match the pink pocket stripe perfectly, they complemented each other well enough. While I'm not sure I was successful, this is the first memory I have of not being too matchy-matchy. Also: side ponytail."

Nancy Einhart, executive editor

You Had a Stylish Entourage

"My school had these fun fair days at the end of every year with games, bake sales, and petting zoos. Of course, my mom dressed me to impress. Acid-wash jeans? Check. Bright blue cardigan tied around my waist? Check. Pomeranian with awesome taste in sunglasses? Hell yeah. And, no, that's not my dog. I'm still not sure who it belonged to (or why it's on my shoulder)."

Kristy Ellington, partner programming manager

You Set the Trends and Didn't Just Follow Them

"This is me dancing around in the outfit I wore to my (very formal) kindergarten Mother's Day [3] tea-party presentation. All of the other kids in my class wore fancy dresses and tights, but I was adamant about this one, despite my mom's plea. During the choreographed part of the presentation where my classmates and I sang about a growing tree, we lifted our arms and I inappropriately bared my midriff. Let's just say the crop top [4] obsession started early."

Sarah Wasilak, Fashion editorial assistant

You Carried a Killer Conversation Starter

"Oof. The plaid. The overalls top. What was my mom thinking?! I'd also like to point out the purple slinky I'm carrying. The ultimate accessory for a '90s child."

Leah Rocketto, Moms assistant editor

You Coordinated Without Going All Matchy-Matchy

"This photo was taken during one of my first days of school in kindergarten. I was a pretty sassy kid, so I obviously loved these zebra-print pants. I remember this as one of my very favorite outfits. Does my pose give that away?"

Stacy Hersher, assistant managing editor

You Didn't Listen to Haters

"My favorite part about this photo is how I accessorized. It's hard to tell, but I have this awesome necklace on that has Scottie dogs made out of wood. The necklace came as a set with clip-on earrings that my mom thought were too tacky for me to wear. (Why the necklace was more OK than the earrings, I still don't know.) I, however, thought the earrings were awesome, so I snuck them to school for picture day to match my necklace. My mom wasn't thrilled when the pictures came in."

Hedy Phillips, copy editor

You Stuck to a Signature Pose

"While I think the laser background is taking too much attention from my chic acid-wash denim jumper (with fetching Peter Pan collar, I might add), I mostly remember learning this pose from the school photographer and later mimicking it in every future picture I ever took. I think I still do it on impulse [5] today."

Kate Schweitzer, Fashion contributing editor

You Paid Attention to Style Icons

"The best thing about having an older sister was getting to dress like her. At school, at home, just about anywhere, I felt infinitely cooler that whatever I was wearing, my big sister was wearing, too. And, to this day, I never met a matching set I didn't like."

Hannah Weil, Fashion associate editor

You Broke Away From Convention

"My dad said, 'Nicole loved headbands; she had one for every outfit.' It's true: I wore a uniform every day until I was in eighth grade, so headbands were my only style outlet. Was obsessed then, still obsessed now."

Nicole Nguyen, assistant Tech editor

You Made Denim on Denim Happen

"I was really owning the kindergarten playground in this jean-on-jean getup. While my mom probably did the shopping, I most definitely did the styling with that cuffed-skirt look!"

Lisa Horten, Moms contributing editor

You Stayed True to Your Roots

"We lived in Austin, Texas, growing up. And even though we moved to California in time for me to start school in 4th grade, I wasn't afraid to get a little – or lot – country with my style. I still love country music and am known to rock my cowboy boots every once in while . . ."

Tara Block, Love & Sex associate editor

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