What to Wear to a Y2K Party

Alison Freer
Alison Freer
Published in
6 min readDec 8, 2016

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Sporty 4 eva.

Remember the 00s? Also known as the two-thousands, or as the Internet calls them: ‘The Aughts’. Which is the worst name ever—it’s basically the Middle English word for ‘naught’, which means ‘nothing’. I prefer the term ‘Y2K decade’, because I loved all the Y2K hype, despite the fact that NOTHING ACTUALLY EVER HAPPENED. It was the late 1990s version of Geraldo Rivera pumping us up for Al Capone’s vault being a bust.

When I was a kid watching the Jetsons, I thought that the two-thousands would come complete with flying cars. Instead, we got communication technology flying faster than His Boy Elroy could have ever dreamed—in addition a bunch of faddish celeb-driven trends that don’t exactly hold up in the cold light of late 2016. For instance: I personally can’t believe I used to leave the house in full open-work crochet clothing like it was just something acceptable to do at 2 pm on a Wednesday.

Your humble narrator at work circa 2001.

A few years back, Refinery29.com interviewed me for a story they were doing about style in the two-thousands. Since they couldn’t use my entire interview in the piece, I thought I’d share it here in it’s entirety.

R29: If you were going to an aughts party, what would you wear? What trends or pieces stand out to you from the aughts?

AF: First, I would pull my T-Mobile Sidekick out of the dresser drawer where it’s been languishing for the past eight years and activate it just for the night. That flick of the wrist when you pulled your Sidekick out was so boss and so aughts.

Paris, Sidekick queen.

The early 2000s were truly the beginning of having an electronic device glued to you 24/7. My career as a costume designer really took off in the years between 2004–2006 due to my ability to look up stuff, reply to emails, and send pictures of costume ideas to my boss faster than any of my peers. In a way, I have my Sidekick to thank for my success.

At this hypothetical aughts party, I’d one-handedly text people on my trusty Sidekick while wearing the crystal encrusted Balmain band jacket from Spring 2009 that an actress gifted me—and carry my favorite lucky ‘FAKE’ Louis Vuitton Murakami bag from 2003.

Left, Balmain. Right, Louis Vuitton.

R29: Do you think any aughts trends or pieces were a flash in the pan, or actually memorable?

AF: Well, that Balmain band jacket had mad staying power. You still see knockoffs of it everywhere. I’m a bag hound, so what really defined the aughts for me was the ‘It Bag’ trend. So many handbags debuted then that you still see around today: The Chloe ‘Paddington’ bag (2003), the Fendi ‘Spy’ bag (2005), the Balenciaga ‘Motorcycle’ bag (2001), and the Marc Jacobs ‘Stam’ bag (2005).

R29: Who or what helped make these trends: the trucker hat, heavily whiskered denim, Uggs?

AF: The aughts were really the start of celebs having the power to validate fashion trends. All it took was a photo of a celeb in a trendy item and suddenly it was poppin’. When Paris Hilton and Nicole Ritchie wore Von Dutch trucker hats on The Simple Life, it instantly boosted the brand into the stratosphere. (I have a dirty denim Von Dutch miniskirt from 2005 that I still wear regularly like the trash hound I truly am.)

Oh, Halle.

I think the fake “whiskered” denim trend was an unfortunate trickle-down effect of the vintage denim craze of 1998–99. There wasn’t enough true vintage denim to go around, and what was available was costly—so by the year 2000, designers just decided to fake it.

I’d try to think of something to say to slam Uggs, but fashion snarking is a dead, boring art. I plastered mine with rock patches and pyramid studs past the point of recognition and still wear them to walk the dog on cold mornings.

2002 two-fer: Headscarf & Uggs.

R29: Were there any fashions from the aughts that you loved?

AF: The aughts were seriously the golden era of Target designer collabs—namely Erin Fetherston, Alice Temperley, Libertine, Luella Bartley, and Tracey Feith. Nothing they’ve done since has come even close. I still have pieces from all those collections that I wear constantly.

Erin Fetherston for Target.

R29: The aughts had this strange mix of futurism and nostalgia. We saw lots of metallics, but we also saw a return to Americana, vintage and selvedge. Why do you think this was?

AF: The rise of metallics in the aughts was likely a nod to the idea that we were entering a fabulous new millennium, but the reality of the September 2001 terror attacks and the following mortgage crisis made everyone crave classic, safe, comfortable looks. Nobody but denim crazed Japanese tourists knew what selvedge was before 2001! Then BOOM, suddenly everyone was rolling up their cuffs to see those good old American made seams.

R29: How did music play into the way we dressed?

AF: The intersection of fashion and hip-hop was absolutely the biggest style story of the aughts. I worked on two dozen Roc-A-Fella music videos from 2003–2007—and still have the Rocawear velour track suits to prove it. Streetwear brands blew up during the early 2000’s—culminating in Jay-Z selling the rights to Rocawear for a cool 204 million bucks in 2007.

Photo courtesy of Refinery29.

By the mid two-thousands, it became de rigueur for fashion designers to be name checked in a hip-hop song.

Cause it’s Louis Vuitton Don night/ So we gon’ do everything that Kan’ like/ Heard they’d do anything for a Klondike — Kanye West, “Stronger”

Aughts-era rappers started lavishing their cash on luxury fashion—and suddenly an entirely new segment of the population became designer clothing consumers. Magazine editors were no longer the only fashion know-it-alls. Musicians (and the music itself!) as arbiters of fashion is true democracy in action.

Follow @Gabriel_Held for non-stop 90s/2000s fashion flashbacks.

R29: Who was the biggest tastemaker during that era? Who do you think defined the time?

AF: Gwen Stefani really blazed a style trail through the aughts. She imported Japan’s Harajuku girls to the states (to the chagrin of some) and in doing so, made the ’FRUiTS’ style absolutely iconic. Her L.A.M.B. line took niche Southern California fashion styles and distilled them into looks that mall shoppers ate right up.

We also have Rachel Zoe to thank for driving boho-chic back into the forefront of fashion on the heels of Cameron Crowe’s Almost Famous hitting theaters in late 2000.

But the de facto tastemaker of the era has to be legendary costume designer Patricia Field. Sex and The City and The Devil Wears Prada defined aspirational fashion in the aughts—period.

R29: How did politics and social movements play into our sense of fashion? 9/11, the recession, reality TV?

AF: I can’t imagine any presidential campaign in the future ever inspiring fashion as much as Obama’s 2008 run did. You couldn’t turn the corner without running into someone wearing a ‘HOPE’ T-shirt.

Also, I was an intensely dedicated watcher of The Hills from 2006–2010—and Lauren Conrad’s classic California style launched a thousand imitators. There is something poetic to me about the fact that when the aughts were officially over, The Hills disappeared with ‘em.

I am the author of ‘How to Get Dressed: A Costume Designer’s Secrets for Making Your Clothes Look, Fit, and Feel Amazing’.

Keep in touch, let’s be pals: Instagram, Facebook, or Twitter! You can also sign up for my email list here or by texting ALISONFREER to 22828. I’ll only send you the cutest stuff, I promise.

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Wardrobe Expert & author of NYT Best-Seller ‘How to Get Dressed’. O.G. mall rat. There’s nothing I haven’t shopped for.