There are perfectly good celebrity style moments, and then there are the looks that really stick with you, the ones you try desperately to recreate at home. In 'Great Outfits in Fashion History,' Fashionista editors are revisiting their all-time favorite lewks.
Gather round, children, and let me tell you a tale about the time during the late '90s and early aughts, when the hottest Vogue-controlled ticket in town wasn't the Met Gala, but an awards show co-hosted and aired live on... VH1.
See, Anna Wintour spent the years between 1995 and 2002 proving she could bring together the hottest stars of film, fashion, sports and music with the VH1 Vogue Fashion Awards. (Think of it almost like the out-of-town rehearsal run of a play before it debuts on Broadway.) And in October 2000, designer Stella McCartney was there, hot on the heels of her must-have Spring 2001 collection for Chloé — you know, the one with all the horse and pineapple prints that dominated both fashion and pop culture for the entire season? Well, naturally, McCartney wore her own design for the occasion: a white strapless dress emblazoned with a giant horse, paired with gold, strappy heels, chainmail earrings, accessorizing further with fellow rock'n'roll royalty, Lenny Kravitz and Liv Tyler.
McCartney beat out other icons of the industry — Tom Ford during his Gucci years, Calvin Klein, Miuccia Prada and Donatella Versace (the year she designed the Google-Image-creating Jennifer Lopez dress, no less!) — to take home the Designer of the Year Award for her work at Chloé. It was presented, naturally, by David Bowie, who pretended to have mislaid her trophy (he offered her instead two tickets to see "Zoolander" when it premiered the following year) so that it can be brought to her by her dad, Sir Paul McCartney, who arrived wearing a T-shirt that read "About flippin time." It was all very, very cute. (Also, spot the brief Phoebe Philo appearance and catch McCartney thanking "Phoebs.")
If you want to get your hands on the Spring 2001 Chloé collection by McCartney, you'll have to join the rest of us in scouring secondhand sites. In the meantime, shop these inspired picks below before you, like me, lose several hours going down a VH1 Vogue Fashion Awards hole on YouTube. (Dear Anna: Put the AWOK on a comeback!)
Please note: Occasionally, we use affiliate links on our site. This in no way affects our editorial decision-making.