Style

The 25 Most Iconic Fashion Moments From the Past 25 Years

Have we really blitzed through a quarter of the century already? 25 years is so long in fashion terms that some trends have already come back around again (frightening for those of us who hoped the diamanté belt and low-slung jeans era was a fever dream). But how did fashion shape our lives over this first quarter? Here’s how we wore it.

(Image credit: Getty Images)

We saw in the millennium (no bugs!) in hip-hugging boot-cut jeans and skimpy, sparkly going-out tops from Jane Norman and Kookai. Over in L.A., Jennifer Lopez wore a jungle-print Versace number and created a whole new movement—not just for scene-stealing red carpet moments, although there is that. Fans’ demand to see her in the dress was so rapacious that it prompted Google to create a function that made searching for pictures online easier. And voila, Google Images was born. It prophetically set the tone for the digital visual dominance which would come to frame the age.

25 YEARS OF ICONIC FASHION MOMENTS

(Image credit: Getty Images)

Britney Spears and Justin Timberlake created a moment for the style annals of all time in their matching head-to-toe denim looks at the 2001 American Music Awards. This was also the year that Juicy Couture released its towelling tracksuit, turning the off-duty look into a serious fashion statement. And then there were the Big Knickers. Thanks, Bridget Jones, for drawing attention to our Spanx.

25 YEARS OF ICONIC FASHION MOMENTS

(Image credit: Getty Images)

Bags heavy enough to cause a hernia became the arm candy du jour with the advent of the It-bag era. Balenciaga’s Le City bag was riding high, as was Mulberry’s limited-edition Gisele Bag by Luella Bartley, which might have weighed a tonne but gained elite status nonetheless, paving the way for the Marc Jacobs Stam, Chloé Paddington and YSL Muse.

25 YEARS OF ICONIC FASHION MOMENTS

(Image credit: Shutterstock)

The Simple Life aired, thrusting Paris Hilton and Nicole Richie into the limelight. Their Rachel Zoe-styled valley-girl aesthetic—kitschy patterned dresses, giant handbags and even bigger sunglasses, no doubt snapped up at Robertson Boulevard boutique Kitson—went global. That’s hot.

25 YEARS OF ICONIC FASHION MOMENTS

(Image credit: Getty Images; Shutterstock)

Two major mood board additions: Kate Moss threw her The Beautiful and Damned-themed 30th birthday party in a midnight-blue sequin vintage dress, and in June, Sienna Miller was papped at Glastonbury wearing a thick embellished belt slung around her hips with (critical detail) a rolled-down pair of classic UGG boots. On the high street, the era of much-hyped high/low collaborations began with H&M’s first designer collection in partnership with none other than Karl Lagerfeld.

25 YEARS OF ICONIC FASHION MOMENTS

(Image credit: Getty Images)

If you didn’t have a “Team Jen” or “Team Angelina” T-shirt, were you even invested in the cultural movement that was Brangelina? W Magazine’s somewhat scandalous shoot set tongues wagging and the Pitt-Aniston divorce cemented a new ‘Sad Jen” rhetoric from the press. Roland Mouret’s Galaxy Dress ascended to icon status, running the celebrity gamut from Cameron Diaz to, er, Carol Vorderman.