I woke up at 6:30 AM, Tuesday, to a fashion crisis. I was standing in front of my closet staring at the same tired pieces I’ve been wearing for years. At that hour, I swear that everything I owned was ugly. I’d written multiple articles about the Y2K trend, and how young people seemed to have fallen in love with the horrible fashion choices I made in my youth. So, I said “forget it,” and pushed aside my neat, plain work clothes to dig through the “Nostalgia Box” I keep at the back of my closet. It’s a pathetic little time capsule of items I can’t bear to give away, but have no use for anymore – mostly from college and my early twenties, that miraculously have endured eight moves and each one of my numerous purges of my wardrobe. The bad news is, that is scary territory.
From the box I pulled out a pair of low-rise jeans. They were True Religion jeans. I know. I wasted stupid money on them ($180) in 2004. To me at 19 years old working part-time at a coffee shop, it was a fortune. The back pockets had huge stitches. Everyone thought they were super cool back then. I think I laughed the hardest.
Miraculously (or frighteningly), they still fit, although I did have to perform some serious contortionist maneuvers and deep breathing exercises. At one point, the button popped off and nearly hit my cat, Rufus. He shot me the worst look of disdain and then sulked off. Rufus is always my harshest fashion critic.
I paired the jeans with a light blue cropped cardigan that fell right above my belly button, a white baby tee underneath (it was free swag from a tech startup) and – I was completely losing my mind – I clipped back the front parts of my hair with butterfly clips. For a grand finale of real 2003-style, I pulled out a handbag shaped like a baguette that I had kept in pristine condition because it was too small to carry anything of value. It barely held my phone, keys and lipstick. Surprisingly, it fit the Y2K aesthetic perfectly – form over function, baby!
When I saw myself in the full-length mirror, I was briefly transported back in time. There she was – College Harper, the girl who believed Uggs were the ultimate innovation in fashion when combined with minis. Now, with the wrinkles around my eyes and the highlights that cost more than my first month’s rent in New York, I’m not exactly sure what I see in there.
Before I got into the rest of the article, I have to admit, I don’t work for a hipster design agency where people show up to work however they want. I work for Style Compass USA. We’re a fashion publication, but we still dress professionally. Our Editor-in-Chief Katherine consistently comes to our team meetings dressed in Prada. However, seeing myself in that ridiculous outfit somehow gave me a lot of confidence. Maybe it was the low oxygen levels from the tightness of the jeans.
Getting to the office was similar to participating in a social science study that no one else agreed to participate in. The security guard at the lobby desk double-checked me twice. The elevator ride was approximately 17 floors of avoiding eye contact with confused consultants from the financial firm below us. When I reached our floor, I was somewhat enjoying the minor disruption I caused.
The first person to notice me was Emma from the digital team. She coughed on her cold brew. “Harper. What. Are. You. WEARING?” she whispered-laughed and pulled me behind a pillar, as though we were co-conspirators in a clandestine fashion transaction. “Those… Oh my god, are those TRUE RELIGION JEANS?! Did you steal from a museum?! Or like, your own teenage bedroom?!”
“Research”, I lied. “That Y2K revival piece. Immersive journalism. I’m getting inside their heads.” This was a complete fabrication. The article was already finished. This was simply pure, mid-week insanity.
Emma looked both terrified and thrilled. “Katherine is going to have a heart attack. You know that, right?”
At no point had I contemplated Katherine’s reaction. Which I suppose indicates just how far gone I was that morning. Katherine Wang, our EIC, is a woman who once sent an intern home for wearing Crocs ironically. She is smart and supportive and has taught me practically everything I know about this business, but she also has strong feelings about what people wear to work. Nevertheless, the idea of Katherine’s disapproval only made the whole situation more thrilling. There’s something about hitting thirty that sometimes makes you want to burn it all down just to feel something. Or, I may have simply needed to add more hours to my therapy schedule.
By 10 o’clock, I had received 17 Slack messages, including “OMG YASSSS!” “Are you okay?” and “Do you need to talk to HR?” The features assistant asked if she could take a photo “for documentation purposes,” which I’m pretty sure meant to document the group chat I wasn’t a part of.
The morning editorial meeting was when things began to get really interesting. I sat in my normal seat, trying to ignore the fact that sitting down in low-rise jeans is essentially an act of public indecency. There isn’t an elegant way to do it. You’re always aware that the incorrect move can result in a plumbing-related incident that no one in a professional setting has given consent to observe.
Katherine entered the meeting room, three minutes late, in the middle of a discussion regarding the cover stories for next month, when she saw me. She stopped dead in her tracks, coffee cup suspended in air, and simply stared. The room was so quiet that you could hear the fashion assistants swallowing in unison down the hall.
“Harper,” she said finally, using that perfectly neutral tone that can signify either approval or dismissal, “that’s quite a bold choice for a Tuesday.”
I launched into my “immersive research” explanation again, adding a term I was fairly certain I created on the fly, “embodied fashion journalism”.
Katherine deliberately sipped her coffee, never breaking eye contact with my butterfly clips. Then, to everyone’s shock – possibly most of all mine – she smiled. Not her press conference smile that never reaches her eyes, but a genuinely human-looking smile.
“When I was 21,” she said, putting her coffee cup down, “I wore a denim mini skirt with a popcorn shirt and those Steve Madden platform sandals — you know the ones with the elastic straps? — to my first magazine interview.”

Everyone gasped. Katherine in anything other than impeccably-tailored designer clothing is like imagining the Queen in jogging suits.

“It was 2002,” she continued, “and I thought I looked incredible. The editor glared at me and said, ‘Darling, this is not Teen People.’ I almost died on the spot.” She paused, seemingly reflecting. “But she still hired me. Said anyone with the confidence to wear that outfit would probably have the chutzpah to cold-call celebrities for quotes. She was correct.”

I hadn’t anticipated Katherine telling a story and, definitely not one that humanized her in a way that left me feeling both more confident and less confident about my fashion disaster.

“I’m not suggesting I support this kind of behavior for client meetings,” she added, waving her hand toward my entire existence, “but it’s nice to remember where we came from. Trends in fashion come and go. All of the things you are currently wearing were fashionable at some point, then less fashionable, now fashionable again. Eventually, they’ll be unfashionable again.”

Then, quickly switching gears to discuss the feature lineup, as if nothing had happened, she left everyone looking a bit dazed.

By lunchtime, news of Katherine’s unexpected endorsement of my Y2K rebellion had spread throughout the office. Three of my coworkers told me they still had items from the era. One confessed to keeping a stash of Juicy Couture tracksuits that she refuses to get rid of. We tentatively discussed planning a “Y2K Friday” that will probably never happen, but sounded great to pretend about.

The biggest surprise came at 3 pm when my social media manager cornered me at my desk. “Wait there,” she commanded, snapping pictures with her camera. “This is pure gold. We’re doing a whole series on employees revisiting the trends they wrote about. Katherine already approved it.”

And that’s how my fashion catastrophe evolved into a six-piece Instagram series that generated more engagement than our Met Gala coverage. The comments section was a funny combination of “QUEEN BRINGING BACK THE REAL Y2K” from teens who were not alive during the original Y2K and “Oh my god no” from millennials who are still traumatized by whale tails and visible thongs.

Honestly, I lasted 9.5 hours in those jeans before I had to change into my backup emergency outfit stored in my desk (black pants and sweater, the fashion equivalent of witness protection).

However, for that brief time, I remembered something I had almost forgotten in the world of “fashionable attire” and “thoughtfully chosen silhouettes” – fashion should be absurd, fun, and generally useless.

Author carl

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