Photo by Ke.Mazur/WireImage, Brenda Chase Online USA, Inc and Evan Agostini/ImageDirect

7 of the most iconic outfits from the VH1 Vogue Fashion Awards

From Gisele's micro miniskirts to Paris Hilton's era-defining 00s style, the Y2K awards show spawned some of the best party looks.

by Zoë Kendall
08 October 2021, 7:00am

Photo by Ke.Mazur/WireImage, Brenda Chase Online USA, Inc and Evan Agostini/ImageDirect

If the Met Gala is where the fashion industry shows out, then the VH1/Vogue Fashion Awards was where it let its hair down. Combining the prestige of the Met Gala with the chaotic energy of the VMAs, the VH1/Vogue Fashion Awards was a televised awards show that ran from 1995 to 2002 and honoured the best-of-the-best of the international fashion industry. Much like the VMAs, the ceremony brought together a motley assembly of musicians, Hollywood actors and, of course, the fashion industry’s top players. And the show’s format was just as varied as its cast of attendees, taking in comedy sketches, runway presentations and musical performances by the likes of David Bowie and Mariah Carey. With some of the era’s foremost fashion icons in attendance, from Devon Aoki to Elizabeth Hurley, the show’s red carpet spawned some of Y2K’s most memorable looks. Think naked dresses, micro miniskirts and bedazzled everything; party-ready outfits to match the night’s revelrous-chic atmosphere. While the VH1/Vogue Fashion Awards is no longer with us, its legacy lives on in the annals of 00s style. Here, we look back at some of the show’s most iconic outfits.

sarah jessica parker posing on the red carpet in a naked dress at the vh1 vogue fashion awards1997
Photo by Ke.Mazur/WireImage

Sarah Jessica Parker, 1997

Who doesn’t remember Carrie Bradshaw’s slinky DKNY dress? It’s the very number that coined the term for the now-ubiquitous “naked dress.” While Sex and the City made the look famous, the dress actually premiered on the VH1/Vogue Fashion Awards red carpet nearly a year before SATC hit the small screen. While shooting the show’s first season in 1997, Sarah Jessica Parker (presumably) borrowed the nude jersey number from Carrie’s wardrobe to wear to the year’s awards show. It was a preview of both Carrie’s and the VH1/Vogue red carpet’s iconic looks to come.

fiona apple posing on the red carpet at the vh1 vogue fashion awards 1997
Photo by SGranitz/WireImage

Fiona Apple, 1997

Fiona Apple’s always been one to march to her own beat. At the 1997 VMAs, the singer-songwriter made her iconic “This world is bullshit” acceptance speech. It was a call for individuality and authenticity in a culture that was becoming increasingly MTV-ized, so to speak. That same year, Fiona attended the VH1/Vogue Fashion Awards wearing one of her most idiosyncratic outfits to date. A statement of individual style if there ever was one, the outfit comprised a prescient mix of of 90s and 00s most ubiquitous trends: mesh on top and a skirt-over-pants combo below, finished off with a swipe of shocking yellow eyeshadow.

gisele bundchen posing in a mini skirt with her vh1 vogue fashion award 1999
Photo by Jim Smeal/Ron Galella Collection via Getty Images

Gisele Bundchen, 1999

During its eight year run, the VH1/Vogue Fashion Awards honoured a wide array of fashion industry figures from designers to photographers to fashion models. In 1998, Steven Meisel won Photographer of the Year; in 2000, Nicholas Ghèsquiere won Avant-Garde Designer of the Year. And in 1999, super-to-be Gisele Bundchen won Model of the Year. Naturally, she scooped the award wearing a turn-of-the-millennium era-defining look: micro miniskirt with a bedazzled choker and belt.

jennifer lopez and p diddy embracing on the red carpet in 1999

Jennifer Lopez, 1999

In 2000, J.Lo (literally) broke the internet in one plunging Versace gown. A year earlier, however, the singer showed her predilection for the navel-grazing neckline on the VH1/Vogue Fashion Awards red carpet. The look was a crystal-encrusted henley dress designed by Tom Ford for Gucci, from the label’s SS00 collection. Coincidentally, that night, Tom Ford ended up taking home the award for Designer of the Year.

gwen stefani posing on the red carpet in bermuda shorts at the vh1 vogue fashion awards 2001
Photo by Evan Agostini/ImageDirect

Gwen Stefani, 2001

Not even a fortnight after dropping No Doubt comeback single “Hey Baby”, lead singer Gwen Stefani took to the VH1/Vogue Fashion Awards red carpet wearing what would become her de facto Rock Steady era look. Pulled almost directly from the song’s music video, Gwen’s VH1/Vogue outfit is pure Y2K rude girl: low-rise bermuda shorts, striped armband and loads of mesh.

brittnay murphy on the red carpet at the vh1 vogue fashion awards 2001
Photo by Evan Agostini/Getty Images

Brittany Murphy, 2001

In true VH1/Vogue Awards fashion, on the 2001 red carpet, actress Brittany Murphy served up not only a dramatic outfit, but red carpet theatrics as well. Drawing from the singular look of the year’s blockbuster musical Moulin Rouge!, Brittany’s outfit is retro-by-way-of-Y2K: a bedazzled flapper-esque dress and kiss-lock bag worn with a pair of the era’s strappy sandals.

paris hilton and nicky hilton posing on the red carpet in matching dresses 2001
Photo by Evan Agostini/ImageDirect

Paris Hilton, 2001

Before there was Paris Hilton’s iconic 21st birthday party look, there was her 2001 VH1/Vogue Fashion Awards outfit. Prior to stepping out in head-to-toe diamante (and chic raccoon eye makeup), the heiress tested the waters by pairing the look’s now-iconic crystal choker (and smudged makeup) with an asymmetric satin gown and baguette purse on the red carpet. A look perfectly befitting of one of the aughts’ foremost style stars, and one of Y2K’s wildest red carpet events.

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7 Iconic Outfits