Exploring The Specific Angst Of Wearing A Y2K Trend The Second Time Around (2024)

It was like something out of a horror movie. I was strolling to the local coffee hatch on a warm August morning when I saw two girls sporting strappy tops and the ubiquitous Samba-and-sock combination. But what really disturbed me was the long, greige puffball skirt also in view.

Suddenly, I was no longer in modern-day London; I was back in 2006, aged 14, getting ready for a party with a vigorously side-swept fringe. I had picked out a puff-sleeved white tee and an oatmeal pinstriped waistcoat to wear with a long string of knotted black pearls, black leggings and pointy heels. My pièce de resistance? A cobalt puffball miniskirt. I loved a puffball skirt. Something about them spoke to me; they were feminine but a little bit off-kilter, bold but not too bold. I have since looked back at the Facebook photos of that night and asked myself: What the hell was I thinking?

I had been warned about this less palatable aspect of the 20-year trend cycle; about how the trends you wore in your youth come back to haunt you. Not least by my mother, whose reaction to me slinging on a tiered white boho skirt and fat coin belt as a pre-teen was: “I wore those in the ’70s, I don’t need to wear them again.”

Of course, the Y2K comeback is nothing new. To make a timely Oasis reference, I have indeed felt the pain of the morning rain soaking my feet through my hundredth pair of cheap ballet flats on the walk to school. Yet, I’ve enjoyed the recent iteration of the ballet flat: there’s something altogether more mature and polished about them than that toe-revealing girlish look of my teens.

So, what is it about the puffball skirt that gives me such a feeling of fashion PTSD? Could I ever bring myself to don a bubble hem once again, or is it one Y2K trend too far for this younger-end millennial?

In search of advice, I reached out to Eve and Bo Brearley of Past Trash, a vintage clothing brand based in Peckham, whose Instagram feed is populated with iconic Noughties ’fits. Born in 1995 and 1998 respectively, the sister duo wore Y2K the first time around: “We grew up keenly saving for second-hand Juicy Couture tracksuits and Abercrombie & Fitch low-rise skirts. Our mum was a Miss Sixty aficionado. We were always raiding her wardrobe.”

The Brearleys note that there’s something important about the way Y2K is being reiterated in contemporary fashion: it’s playful, it’s creative, it’s fun. It’s this general unseriousness of the 2020s take on the nostalgic decade that jars with my memories of wearing these trends the first time around. Because back then, when I was 14, it all felt – well –really serious. The sisters advise starting small and coupling Y2K pieces with items I already have in my wardrobe, as per the mix-and-match style that’s popular now.

I fear there is nothing “small” about the puffball skirt, but I begin to envision how it might look pared down with something sleeker than an oatmeal waistcoat and black pearls. The Facebook photos haunt me, because I know that that night, I thought I’d put a look together that was daring. I’d borrowed the waistcoat from a cooler friend; I’d angsted over whether to wear the leggings or a pair of over-the-knee socks. I was trying to make a statement, but fashion still felt like a language I was failing to speak. Back then, there were no TikTok how-tos on styling the latest “-core”. There was no Instagram. You had to parse the pages of fashion magazines and celebrity paparazzi shots, Topshop campaigns and Abercrombie catalogues, to understand what was de rigueur – and then you had to try to recreate it in your bedroom mirror. There was no FaceTiming your bestie for a ’fit check before you went out; you simply had to turn up to the party and pray you’d got it right. For someone who spent most of her childhood dressed like ’90s Liam Gallagher, girly asymmetric hemlines weren’t fun; they were a matter of social life and death!