The writer in high school—not wearing Tommy Hilfiger overalls.

When I was in Grade 9, what I wanted most—more than good grades (yes, I was kind of a nerd) or even the affection of a super popular skater boy (not a chance; nerd, remember?)—was a pair of Tommy Hilfiger overalls with the brand’s logo emblazoned on the straps. Destiny’s Child had rocked the look two years earlier, so I was a bit late to the trend… but I was in love. There was just one problem: they cost, like, $200 so when I *oh so casually* floated the idea past my parents, already knowing the answer but unable to resist trying, I (unsurprisingly) got a hard “no.” I was allowed to get other, much less expensive overalls, but they just weren’t the same.

Eventually, I made peace with the fact that me + Tommy Hilfiger overalls were not to be. Plus, trends changed, so soon I was lusting after very, very low-rise jeans and handkerchief tops à la Christina instead. But I never forgot about the first item of clothing that I really wanted and, sadly, never got. Fast forward several (OK, 19) years and those Tommy overalls are back (!!!). But while I still think they’re pretty chic, I don’t feel the same overwhelming need to own a pair… Which got me wondering about my colleagues’ unrequited sartorial loves from their high school days, and how they feel about them now. So, I polled the office to find out what everyone else’s most-coveted fashion item was and, reader, I’m not sure you’re ready for the nostalgia.

“If an illegal knock-off was the only way I was going to get a Von Dutch hat, I was willing to accept it”

Laura posing behind a McDonald's drive-thru sign with a friend. She's wearing her knock-off trucker hat

“In my mind, there’s only one accessory that perfectly encapsulates the fashion of the early 2000s: Von Dutch trucker hats. Worn by everyone from Paris Hilton to Nicole Richie to Britney Spears and even Madonna, they were the coolest of the cool, and I needed one.

But in 2004, when I was 14, I couldn’t afford a Von Dutch trucker hat. They cost upwards of $45 (some were over $125!!), which was a lot of dough for someone whose only income was babysitting for $5 an hour. I begged my mom for one, but she thought their price tag was outrageous and refused to spend her hard-earned dollars on a cap made mostly of mesh. She did, however, offer a solution: she would pay $20 for a knockoff camo print one that her friend found at a convenience store in a sketchy strip mall. If an illegal knock-off was the only way I was going to take part of the hottest trend, I was willing to accept it.

Even though my knockoff Von Dutch cap wasn’t the real deal, none of my friends could tell, so it was all the same to me. Plus, I felt super edgy wearing the same hat as Christina Aguilera.” — Laura Hensley, staff writer

“I remember coveting a super expensive velour Juicy Couture sweatsuit”

Ishani posing in print of an open closet. She's wearing flared jeans and a pink t-shirt.

“I was in the same school for both middle and high school. It was a private school and we were required to wear uniforms, but on ‘civvies’ days people went all out. And by all out, I mean they wore the chicest form of grunge on offer. Most of the girls in my school were fairly well off, so I remember coveting the super expensive velour Juicy sweatsuit. They were not cute at all, but the fact that they were so out of my reach made this matching ensemble more desirable.” — Ishani Nath, acting senior editor

“I was both behind the times and way ahead”

“My must-have clothing item in high school was a pair of pink Phat Farm shoes, the brand to wear when it came to sneakers as I was entering high school in 2005. Actually, I was a little behind the times, but regardless they were still cool. While I cringe at most of my clothing choices back then—hello, pastel Lacoste polos and low-rise jeans—these were honestly the early-2000s version of the currently en-vogue Adidas white sneaker. So, I was both behind the times and way ahead.” — Meaghan Wray, digital editor, HELLO! Canada

“Everyone in my friend group had a TNA sweater (in different colours, obvs)”

A group photo of five teens. Erinn is in the middle; she has long, wavy brown hair and is wearing a grey TNA hoodie over a white t-shirt

“I was in high school when Lululemon and Aritzia started becoming a thing. All of the cool girls in my dance class (read: rich, private school girls) wore Scuba hoodies and TNA zip-ups, which meant I had to have these items, too. I went to a Catholic school and had to wear a uniform every day, but I layered my trusty purple TNA sweater over my ugly polo shirt to and from class. Everyone in my friend group had the sweater (in different colours, obvs) and even though mine was donated years ago, I’m still reminded of the ‘good old days’ whenever I see one on the street.” — Erinn Stewart, assistant fashion & beauty editor

“I found a pair of bellbottoms at Stitches and wore them until they disintegrated”

A high school grad photo of Lora. She has chunky highlights and is wearing a graduation gown and holding a diploma

“I was completely obsessed with the pants Janet Jackson wore in the ‘Doesn’t Really Matter’ video (watch the dance break at 2:00 to get a good view!). Tight tops and baggy pants were so0o0o in at the time and Janet looked so badass in the video. In Grade 9, I found a pair of bellbottoms at Stitches (lol) that were skin-tight around the thighs and then flared out at the knees—they even had their own belt. I wore them until they pretty much disintegrated.” — Lora Grady, senior fashion & beauty editor, Walmart Live Better

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