I was standing in front of my closet cursing at my outfits options at 6: 30 a.m. on a Tuesday morning when it hit me. You know those Mondays when your entire closet suddenly looks like thrift store rejects and you’re sure your colleagues can tell you’ve been wearing the same three jackets for the last five years? Well, it was like that, but on a Tuesday.

For months I’d been writing about the Y2K comeback for Style Compass USA, diving deep into how Gen Z loves all the fashion trends we millennials definitely screwed up the first time around. But that morning, as I surveyed my embarrassingly slim selection of work-appropriate clothing, I caved. “I don’t freaking care,” I said out loud, rifling through my trusty “throwthingsintheclosetandforgetaboutituntilinanxietyattack” box.

This catch-all hadn’t seen the light of day since my college move-out day six years ago, and was essentially a shoebox full of emergency grains-sized clothing that I either couldn’t fit into or deeply missed. aka panic hole. Digging through the cramped space, I unearthed a pair of low-rise jeans I had optimistically hung onto since graduation. (True Religion, if we’re being honest.) I think I paid $180 for them in 2004.

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To me, at the time, it was INSANELY expensive.

I only worked part-time at a coffee shop, but damn did those jeans feel like $180.

The back pockets were embellished with these massive gold stitches that made them extra bulky, which we all thought was stylish back in the day. Oh, Anthropologie dressing sets, how we mocked you.

Thankfully (to my butt cheeks, at least), they still fit, after about half an hour of squeezing and wiggling and straight-up holding my breath. I even lost the button at one point, nearly jabbing my cat across the face with it. Rufus eyed me menacingly and sauntered away; he’ll never forgive me for those skinny jeans.

He still refuses to sleep on my newly-postgrad-with-money-bed because of it. After struggling into my denim disgrace wrap around them with a cropped baby blue cardigan that stopped right at my belly button, a crisp white baby tee I plundered from the depths of my office random free merch bin (thanks, Silicon Valley tech startup newsletter company! ), and ; because we’re clearly going down hill from here ; some sweet butterfly clips to section off the front halves of my hair. To top it all off, I grabbed a tiny baguette purse that could barely fit my wallet, let alone a smartphone.

In retrospect, not being able to put my cellphone in my purse was pretty on-brand for a Y2K revival. As I stared at my full-length mirror image hovering ominously over my IKEA dresser, I caught sight of myself. There before me was college-aged Harper, ready to take on the world and fully believing that pairing Uggs with a mini skirt was a good idea.

Only now she had laugh lines, and expensive bangs. Full disclosure: I do not work at an editorial company where we can show up in lounge trousers and call it “expressing ourselves”. Yes, Style Compass USA is a fashion magazine.

But we still have standards. Like how my EIC Katherine sports Valentino almost every time she comes into the office. FOR REAL.

But against my better judgment, I felt… free? Maybe it was just myIO2 deprivation talking. Slowly I descended the stairs of our New York office, playing bridal death march whilst avoiding eye contact with anyone.

The security guard at the lobby station did a double take so violent, I thought he’d pulled a hamstring. I spent my lift ride mentally preparing weak excuses for my colleagues in the financial firm downstairs as we rode up 17 stories together without speaking. By the time I reached our floor, people were actually stopping to watch me saunter by.

It wasn’t until Emma from digital saw me first and coughed violently on her oat milk latte that people actually started reacting. “Harper. What.

WHAT ARE YOU WEARING?” Emma squeaked, ushering me into the nearest alcove. She looked at me, eyes wide, as if she were struggling to comprehend the outfits’magnitude. “Are those…holy shit.

Are those TRUE RELIGIONS?! Did you steal these from a museum? Or like, your childhood bedroom?” “It’s for research,” I told her defensively.

“For my Y2K comeback story. I’m doing…research, journalistic immersion?” Girl please. I already wrote and scheduled that story.

Hell hath no hold for Tuesday outfit madness. Emma shook her head, eyes still glued to my waist as if she could somehow unravel the secrets of the jeans’hold on my hips by staring hard enough. “God, Katherine is going to have a heart attack.

You know that, right?” Meandering my way through our office that morning, I was bombarded with stares and selfies; at one point our features assistant even asked if she could take “official photos for the archives.” She winked when she said it, which I’m pretty sure meant “to post on Slack where you’re excluded.” Our fashion closet team cheered when I popped by to return a sample they hadn’t needed; maybe they were cheering UNDER my skirt? It wasn’t until our morning editorial meeting that I truly felt the weight of my jeans apocalypse. Making my way down the hall to touch-graze my knees together at my desk, I braced myself against the shame radiating from my fellow editors.

Sitting down in low-rise jeans is basically a public indecency, and unfortunately for me, there’s no sexy way to do it. Part of you is always clenched, waiting for the other half to betray you and your childhood dreams. I took my seat as Katherine breezed through the door, two minutes late and ranting about cover stories for next month.

She paused mid-sentence, coffee suspended halfway to her mouth, and looked at me. She stared. A pregnant silence fell over the room, you could’ve heard our fashion assistants gulp softly across the hall.

“Harper,” she said softly, with that deadly tone we’ve all grown to fear and love in equal parts. “This…is a new low, even for you.” I screeched into my “I came up with this whole methodology out of thin air” story again, chalking it up to some sort of “engaged journalism.” Maybe even “learning through embodied understanding” If something like that actually exists. (It does not.) Katherine took a careful sip of her latte, studying me through her spectacles. She set the mug down so slowly I thought she was going to add it to the lecture.

And then. She smiled. My editor.

Smiled at me, sitting in those jeans. She smiled! ! “I was 21 when I wore this denim mini skirt with a popcorn shirt, and THOSE Steve Madden platform sandals with the criss-cross straps,” she began, cupping her hands together so we could all get a good look at her past fashion sins.

“? ; to meet with my very first magazine editor. It was 2002, and I thoughtI looked fabulous.” The entire office collectively gasped. Katherine Wang in non-Vogue-worthy clothing was like imagining Beyoncé rocking sweatpants.

“But my editor looked at me and said, ‘honey, this ain’t nobody’s Teen People cover.’ I wanted to die.” Katherine paused, twirling a strand of hair thoughtfully between her fingers. “But she hired me. Said if I could rock up to her office like that, I was brave enough to probably pick up the phone and call celebrities for comments.

She was not wrong.” Had Katherine just told us all a story about how brave she was dressed at 21?!!? Me, feeling kinda vindicated about my unintentionally clever choice. “Not saying I’d invite you to meet with clients like this,” she waved vaguely at my general vicinity, “but it’s always good to remember why we fell in love with fashion in the first place.

Trends come and go. Whatever you’re wearing was high fashion, trash, and back in style again. Before you know it, it’ll be on the out end of the cycle.” She winked at me when she said it.

Jesus Christ, she supported me wearing THESE jeans? And just like that, she turned on her heel, briskly walking us through the morning’s features before anyone else could comment. She SAID IT WAS FINE AND WE WERE ALL JUST GOING TO MOVE ON WITH OUR LIFE?!

WHAT. By lunchtime, rumour had spread throughout our office that Katherine had blessed my outfit firsthand. Three other staffers pulled me aside to confess they STILL owned things from Y2K; one woman even admitted hiding her Juicy Couture tracksuits in her basement (“Like Hulk hides his green sweats!”).

We made plans to theme our next office Friday around Y2K attire, which we all secretly knew would NEVER happen but enjoyed pretending we could.

My surprise came two hours later when our social media editor blocked my path to the coffeemaker.

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“DON’T MOVE,” She hissed, whipping out her iPhone.

“This is content GOLD, girl. We’re literally doing a whole video series on employees revisiting trends they wrote about coming back. Katey already approved you.” Thus, was born a six-part Instagram documentary following me around for a day in my decidedly NOT-work-appropriate outfits.

The comments ranged from ” BRING BACK TRUE Y2K FASHION !” from teens who weren’t alive the first time around to. “NOPE” from millennials who STILL remember walking sideways into rooms to avoid flashing everyone around them. Will I be daring enough to pair my old LJ froms Hollister top with leggings for work?

Heck no. My organs have not yet recovered from the trauma of those jeans. But for a few hours that Tuesday morning, I felt freed from the expectations of what it meant to “dress for the office.” Clothes can be silly, and wonderful, and shouldn’t always have to make “sense.” P.S.

I will never wear those butterfly clips again. Deal with it, Past Me.

Author carl

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