Fashion Regrets: 12 Things We Thought Were Cool in High School

“It was a different time.” “I had an underdeveloped sense of style.” “All the kids were doing it.” We can make a lot of excuses for the ways we dressed in high school, but nothing truly explains the style aberrations that defined our adolescence. From ridiculously high platform flip-flops to the trusty combo of a velour hoodie, denim miniskirt, and shearling booties, scroll down to check out the high school fashion moments we’d rather forget.

“I wore loads of cringe-worthy things in high school, but the ultra-chunky platforms I used to adore are definitely the worst. They were so hugely high—a six-inch heel (plus a platform in front) was normal—and ridiculously heavy, I could barely lift my feet. I’m sure I looked like a Clydesdale horse clomping around in them, but for some reason I thought they were the coolest.” –Hillary Kerr, Co-Founder & Co-CEO, Clique Media

“I was a huge fan of those tank tops that had the built-in bandeau sports bra. Perhaps because I was a blossoming woman, I found them practical, comfortable, and attractive. They were certainly at least two of these three things.” –Meghan Blalock, Managing Editor, Who What Wear

“I thought it would make me better at hip-hop to wear Cross Colours—I was more of a ballerina but I tried. I had the snap crotch, hooded bodysuit, and all of the different coloured shin-length baggy shorts. Yikes!” –Katherine Power, Co-Founder & Co-CEO, Clique Media

“At my high school, the cool girls wore ridiculously high platform flip-flops, so I decided to get a pair, too. The second day I wore them, I tripped during passing period. Somehow, my toe got caught in the strap, and the shoe wouldn’t come off! A guy friend walking by had to use a pair of scissors to snip the strap right off my foot. I did not buy a new pair, and have stayed away from platforms of any kind ever since.” –Tiffany Tse, Deputy Editor, Clique Media

“I used to think it was entirely fashionable to pair my shearling booties with mini denim cutoff skirts and velour tracksuit hoodies. If I felt especially sassy, I'd throw a few butterfly clips into my hair for good measure. Looking back, this is just all kinds of wrong.” –Alex Taylor, Director of Content & Social Strategy, Clique Media

“I used to take my dad's ties and wear them around my waist as belts. Think less street style bait, more child mob boss.” –Nicole Kliest, Senior Editor, Who What Wear

“I was really into ~*sk8r boys*~, so I bought and proudly wore skater shoes—the big puffy ones that no one (not even skateboarders) should really wear. Luckily, I think people were too distracted by my large hoop earrings to pay attention to my footwear.” –Sarah Chiarot, Junior Art Director, Clique Media

“I went through a stage where for some reason I thought the Playboy insignia was really cool. I had a visor, a polo shirt, even a vintage bomber jacket. That one was actually kind of cool.” –Meghan Blalock, Managing Editor, Who What Wear

“In high school, I had a misconstrued notion that walking around with a brand's name on my butt was the epitome of coolness—especially if they happened to be emblazoned on flared sweatpants (shudder). The pants would usually stretch throughout the day, and by the end of seventh period, I would have major saggy-sweatpants-butt syndrome going on. But I didn't care. My behind and Juicy, Hollister, and Abercrombie were a match made in heaven, and nothing anyone said or did could tear them apart. The eventual breakup, thankfully, was amicable—we simply grew apart as my butt found more suitable partners that didn't have to always be the center of attention.” –Faith Xue, Editor, Byrdie

“I used to love wearing this one Abercrombie & Fitch graphic tee that said ‘Hula Lessons’ on the front, and ‘It’s all in the hips.’ on the back. I wore it to a school dance once—I suppose so everyone would notice my scintillating hip-swinging.” –Kat Collings, Editor, Who What Wear

“Growing up in the heart of the Bible Belt, sparkly cross necklaces were a legitimate trend and a religious accessory, which only gave the trend more weight. I, too, participated.” –Meghan Blalock, Managing Editor, Who What Wear

“I had a pair of silver pants that I most likely purchased from Wet Seal. They were way too long for me and basically awful, but I thought I looked so cool in my weird space pants that I even wore them to my sophomore year Sadie Hawkins dance.” –Allyson Payer, Executive Assistant to Katherine Power, Who What Wear

Do you have any high school-era fashion regrets? Share yours in the comments below!

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