10 Looks That Prove 2000 Was The Decade's Best Year For Golden Globes Fashion

Even if you're not fond of celebrity culture, there's still a good chance you've tuned into an awards show to see what the glitterati are wearing. After all, there's nothing quite like being cuddled up on the couch in your pajamas while judging the outfits of people who make far too much money. Especially if those people are like Blake Lively, who desperately needs a legit stylist, despite being adamant that she doesn't. Oh, the sweet satisfaction that comes from a celebrity you don't like having a fashion fail.

While each year has its fair share of winners and losers, fashionably speaking, the 57^th Annual Golden Globes in 2000 proved to be the decade's best year for Golden Globes fashion. As the '90s came to a close and Y2K fashion started to take hold, looks were all over the place; some celebrities stuck to classic Hollywood glamour, while others leaned into the trends of the time. Gwyneth Paltrow, for example, went full Y2K that night, and we love her for it.

Although all awards ceremonies are unique in their own way, the Golden Globes remain the most fun. Not only do you have both film and television stars coming together, quietly competing for best dressed, but with the free-flowing Moët & Chandon (the official beverage of the Golden Globes for the last 30 years), there's always a chance that someone is going to get drunk and make a scene. Drunk celebs in haute couture make for great TV.

In both 1996 and 1998, Sharon Stone showed the world that you actually can wear a top from the Gap to the Oscars — as long as it's paired with a designer skirt. For the 2000 Golden Globes, Meg Ryan took a page from Stone's red carpet history by wearing a casual short-sleeved gray top with a full-length yellow skirt. Not only did Ryan look incredibly comfortable, but the versatile outfit really stood out because it was just as appropriate for the Globes as it would be for a Friday night out.

When we see this photo of Mariska Hargitay, we do have to wonder: did she think she'd still be playing Olivia Benson on "Law and Order: SVU" a whopping 26 years later? Although the ageless beauty, even when going makeup-free, wouldn't win her first Golden Globe until 2005, she dressed like a winner in 2000. In a black-panel sequined gown with a modest train and matching shawl, Hargitay absolutely stunned. So much so that we can forgive the light blue eye shadow, a '70's trend that we hope never comes back.

For the 57th annual Golden Globes, Angelina Jolie took home the award for Best Supporting Actress for her performance in "Girl, Interrupted," while wearing a full-length white silk slip dress. Jolie completed her look with an oversized matching blazer, nude heels, and a few strands of diamonds around her neck. Although it's one of Jolie's outfits that didn't work because the color washed her out, in 2000, when slip dresses had become all the rage throughout the 1990s, it was the perfect choice for the event.

In 2000, John Galliano, while creative director for Christian Dior, presented one of the most controversial collections in recent memory: a line inspired by the unhoused population of Paris. Then, for the 2000 Golden Globes, Courtney Love, who loves controversy, wore one of Galliano's gowns made of twine, 'a book of matches, glass, [and] all this taxidermy,' Love told The Guardian in 2019. While the inspiration then is just as shocking and offensive now, when the Queen of Grunge music walks the red carpet in a dress like this, it just makes sense.

Halle Berry was only 34 when she secured her first Golden Globe nomination and win for her performance in "Introducing Dorothy Dandridge" in 2000. For the big night, Berry wore this lacy white and red Valentino gown with matching heels. Berry, who would go on to become one of our favorite celebrities who doesn't play by society's beauty rules, really leaned into the lace trend for the event. While today it might be considered a bit frumpy, in 2000, as grunge was wrapping up, boho chic, including frills and lace, was already underway. 

Just when you think only Kate Middleton knows how to turn a pantsuit into a sleek fashion statement, this photo of Lara Flynn Boyle in a tailored suit at the 2000 Golden Globes pops up and gives Middleton some serious competition. Although pantsuits with a baby (sequined!) ringer tee underneath have never been particularly common at awards ceremonies, Boyle absolutely slayed in this outfit, while staying true to the fashion of the time. She completed the look with black heels and minimal makeup, because when you're this chic, you don't need much else.

Although Sarah Jessica Parker has some outfits that should be on the worst-dressed list, the gown she rocked at the 2000 Golden Globes isn't one of them. For the event, Parker wore the embellished pale-pink dress by Richard Tyler, serving major princess vibes. Unlike some celebrities who keep their natural curls under wraps, Parker let her locks free, à la Carrie Bradshaw. That night, Parker took home the Globe for Best Actress in a Television Series for "Sex and the City," of course, making it the first of six Golden Globes she'd win for SATC.

If you need more proof that 2000 was the decade's best year for Golden Globes fashion, look no further than Gwyneth Paltrow. Not only did Paltrow trade in her famous blond hair for near-black, but she also wore black pants, a yellow cowl neck top, and sandals to the event. As if to offset the casualness of her outfit, Paltrow wore chic gold cuffs, dangly earrings, and a layered necklace. Having won the Globe and Oscar in 1999 for "Shakespeare in Love," maybe Paltrow figured this was her chance to relax.

Thanks to her phenomenal performance as Brandon Teena in 1999's "Boys Don't Cry," Hilary Swank quickly became a breakout star and a household name. She was nominated for her portrayal of Teena, and won her first Golden Globe in 2000 while wearing a black beaded and bedazzled Versace gown that happened to be on the sheer side. Although decades before the sheer dress trend emerged, in 2000, Swank showcased exactly how to ace the sheer outfit look flawlessly. We love a woman who's ahead of her time.

Although Calista Flockhart, who was starring in "Ally McBeal" when she attended the 2000 Golden Globes, tends to fly under the radar when it comes to her red carpet looks because she usually plays it safe, that wasn't the case in 2000. Flockhart, a celebrity who rightfully forces us to confront our fixation with age-gap relationships, absolutely brought her Y2K A-game to the 57th Annual Golden Globe Awards. Wearing a full-length black sequin and lace gown with capped sleeves and a choker — the ultimate jewelry accessory of the time — Flockhart was picture perfect.