Millennial Woman Voted ‘Best Dressed’ In High School Shows Off ‘Humiliating’ Outfits That Earned Her The Title
T.Den_Team | Shutterstock Millennial fashion truly was something else, as evidenced by a woman who shared the looks that earned her the title of “best dressed” in high school.
In all fairness, each generation develops its own unique look that makes people from other age brackets scratch their heads. And trends change over time, of course, so something you thought was super stylish 10 years ago might make you cringe now. These truths don’t make it any less amusing to look back on outfits in old photos and wonder what in the world someone was thinking, though.
A millennial woman who was once considered ‘best dressed’ at her school was able to poke fun at the outfits she would never dream of wearing now.
In a TikTok video that had people basking in waves of nostalgia, musician Perenna King showed some of the outfits she regularly wore in high school that not only made her feel like a million bucks, but also caught her classmates’ attention so much that they awarded her the “best dressed” superlative.
First up was an absolute classic. A younger King was wearing a light pink top that had a neckline with a deep scoop, which she made school-appropriate with a white tank top underneath. The staple of the look was a large, ornate pearl necklace, which she said was actually attached to the shirt.
Statement jewelry seemed to be a theme for King, as did bright colors that didn’t always quite match and layering multiple tank tops. One photo showed her in a short bodycon-style romper that left her asking, “Girl, what are you doing, and who are you doing it for?”
Perhaps the most iconic outfits for people who remember that era were a pink shirt accented by a chunky white belt around King’s abdomen (no, not her waist) and a pair of jeans with suspenders over layered tank tops with an eye-catching pink scarf. “You couldn’t take skinny scarves away from me,” she insisted.
King may have been embarrassed by her high school fashion, but other people couldn’t get enough of it.
In the caption of the video, King wrote, “Skinny scarves, belted shirts, over accessorizing. I really thought I was IT, huh?” Commenters confirmed that she did, in fact, have major it-girl energy.
“Class of 2006 here and I’d still vote you best dressed,” one person said. “I was there and I think your outfits were top-notch!” another stated. A third noted, “Honestly, you slayed.”
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Several people also compared King’s style to popular celebrities from the time, and they were honestly spot-on. “But [at] the beginning of this video I thought you were Demi Lovato,” someone insisted. “You kinda looked like Kesha in the metallic romper,” a second person commented. A third declared, “It’s very Kate Middleton before marrying Prince William.”
Millennial fashion has evolved a lot, but that doesn’t mean we need to ignore memories of the more interesting looks.
As an older Gen Zer who feels a bit more like a millennial, I remember these trends well, and I wore many of them myself. I can laugh at these outfits as they remind me of a specific time from the past, but I can’t really make fun of them, knowing how cool they made us all feel.
Millennials were known for wearing apparel like skinny jeans, giant scarves, cardigans, and boots that could either come up to the ankle or the knee that they bought from stores like Old Navy, Forever 21, American Eagle, and H&M. And, if that doesn’t make you want to take a trip to the mall, I don’t know what will.
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While millennial fashion may feel like a joke now, there’s no denying that it had a massive impact on culture. This generation is continuing to make its mark on the fashion industry, albeit in updated outfits. Vogue reported that 19 fashion brands named new creative directors in 2025, and 13 of them were millennials.
Looking at old pictures may make you cringe, but there’s nothing wrong with celebrating what was once important to you. Those outfits that feel embarrassing now used to be what gave you confidence, and that’s worth remembering.
Mary-Faith Martinez is a writer with a bachelor’s degree in English and Journalism who covers news, psychology, lifestyle, and human interest topics.
