As far as red-carpet fashion is concerned, the years between 1999 and 2009 were some of the very best. We saw some of the biggest stars of the era, including Jennifer Aniston, Penelope Cruz, Kate Hudson, Keira Knightley, Beyoncé Knowles, Sarah Jessica Parker, and Reese Witherspoon, rock fashion that would go on to stun us for another decade, and beyond.
The most iconic looks of this time are the ones we still talk about today, whether they were good or bad. They’re the ones that experimented with fashion and had their risks paid off. And they helped to cement the stars wearing them as style sensations and fashion gurus. To this day, they go down in the fashion hall of fame.
The Academy Awards, The Golden Globes, The Screen Actors Guild Awards, The Emmys, and The Grammys were the scenes of the biggest moments in fashion between 1999 and 2009. Whether the celebrities went on to win big or not makes no difference as to how well we remember the fashion, or whether or not they’re style icons.
So which looks in the ten years between 1999 and 2009 were the most memorable, the most stunning, and above all, the most iconic? Keep reading to find out!
25 Gwyneth Paltrow In 1999
To kick off our list, this 1999 look from Gwyneth Paltrow is a classic. She’s in a pink gown by Ralph Lauren at the Academy Awards, and we think this is perhaps the first time she made a name for herself as an icon of style.
Everything from the makeup to the hair to the jewelry screams glamour and sophistication. And honestly, it's been a while since we’ve seen Paltrow in this pretty color, but we think it suits her exceptionally well.
24 Jennifer Aniston In 1999
Friends was at its prime in the late 1990s, and any member of the cast could have turned heads on any red carpet, even if they were dressed in a potato sack. But Jen exceeded expectations.
We love this sequin embellished Saint Laurent dress that Jennifer Aniston, who plays Rachel Green on the show, wore to the Emmy Awards in 1999. Her hair is a far cry from "the Rachel" or from the Aniston we know today, but it is so ‘90s and we love it!
23 Celine Dion In 1999
Who said that our favorite red carpet looks had to be gowns? This backward tuxedo by Christian Dior has to be one of the most memorable looks by legendary singer Celine Dion. She rocked this fierce, all-white look to the 71st Academy Awards in 1999, and with the matching hat and sunglasses, was perhaps going for the “I’m too cool to be here” look.
We are not too sure that anybody else in the world could get away with this, but Celine Dion knows how to make it iconic.
22 Halle Berry In 2000
The turn of the millennium brought with it some even more stunning red carpet looks for us to drool over. Here is Halle Berry at the Emmy Awards in 2000, wearing a Valentino gown that would end up being one of our favorite Berry looks ever.
The strapless bodice with the flouncy skirt oozes fairytale glam, and when done well, black is one of our favorite colors to see on the red carpet. We also think that gold Emmy award complements the dress perfectly.
21 Bjork In 2001
This famous dress might not be on every fashion critic’s wish list, but it did make history. Thanks to its influence, it is an iconic piece, whether it makes you gag or not.
Singer Bjork donned this dress and certainly made a scene at the Academy Awards in 2001. It was designed by Marjan Pejoski and was made to look like the singer had a swan around her neck. In 2015, the dress was featured in New York’s Museum of Modern Art.
20 Jennifer Garner In 2002
Returning to dresses that we do wish we had in our closets, this beauty was worn by Jennifer Garner at the Emmy Awards in 2002. Isn’t it divine? The pale Ralph Lauren gown is the epitome of elegance, combining the simple style with the simple color to create understated perfection.
The diamonds around Garner’s neck add a hint of opulence and complement the effortlessness of her messy up-do. Garner certainly knows how to get it right on the red carpet!
19 Sarah Jessica Parker In 2003
By 2003, Sarah Jessica Parker had already established herself as a certified fashion guru and was starting trends that would go on to be worn by women around the world. At the Emmy Awards that year, as her hit series Sex and the City was nearing its final days, Parker decided to rock this pink Chanel gown and caught everyone’s eye.
Paired with slicked back hair and just enough jewelry, this look went onto become one of Parker’s most iconic and most talked about.
18 Kate Hudson In 2003
We love seeing that bohemian spirit come out on the red carpet! How to Lose a Guy in 10 Days actress Kate Hudson wore this Valentino gown to the Golden Globe Awards in 2003 and turned heads for all the right reasons.
Prints don’t always translate well on the red carpet, but in this case, Hudson looks exquisite. We think her loose golden ringlets look made for the gown, which somehow manages to be relaxed and chic at the same time.
17 Gwen Stefani In 2004
Even rarer than print on the red carpet is a gown with a turtleneck. When Gwen Stefani showed up to the Golden Globes in 2004 wearing this white mock turtleneck dress by Jean Paul Gaultier, a lot of critics didn’t know what to think.
To us, Stefani pulled this look off well and made the style seem modern. The signature red lip helped Stefani to really make the look her own and brought a touch of elegance to the white ensemble.
16 Jennifer Aniston In 2004
Of course Jennifer Aniston makes our list twice! It wasn’t her arm candy that made her stand out at the Cannes Film Festival in 2004 (although being part of the biggest power couple of the era no doubt helped!).
Aniston opted to go against her norm this year, and instead of wearing her signature black, went for this paneled white satin dress by Valentino. Pairing it with the hairstyle she had made famous was a good move and helped make this look one of the actress’s most iconic.
15 Charlize Theron In 2004
Jennifer Aniston wasn’t the only fashion winner at the Cannes Film Festival in 2004. Charlize Theron blew us all away with this pale Dior number that had commentators talking for days. Critics were divided, with some finding the gown a little too unorganized and others believing it to be heaven-sent.
Whatever camp you’re in, nobody can deny that Theron looks beautiful in just about anything. Few people could get away with the pale shade of the dress, but Theron does.
14 Hilary Swank In 2005
It’s been over ten years since this iconic fashion moment, but we’re still frothing at the mouth over Hilary Swank’s look at the Academy Awards in 2005. This backless midnight blue gown by Guy Laroche made Swank look like a true movie star and was the perfect way to celebrate the months of hard work that went into training for her demanding role in Million Dollar Baby.
The color, the makeup, and the fact that this dress is so different from the norm all make this look one of our favorites.
13 Michelle Williams In 2006
The saffron color of this gown is another fashion risk, but going for it certainly paid off for Michelle Williams. After rocking this stunning gown by Vera Wang to the Academy Awards in 2006, Williams became a fashion icon overnight.
We love everything about it, from the color to the creative style to the way she enhanced the look with a pop of red on her lips. Williams couldn’t have won at fashion on this night any more than she did!
12 Keira Knightley In 2006
Strapless gowns have been done before, but they’ll never be totally out. This Valentino dress that Keira Knightley wore to the Golden Globe Awards in 2006 is another look we won’t be forgetting any time soon.
The bow on the front saves it from being just another strapless white gown that could be confused for a wedding dress. Though the Pirates of the Caribbean actress elected to leave her neck totally bare, she did enhance this look with some dazzling pieces on her wrists and ears.
11 Penelope Cruz In 2007
We’ve tried to get over this blushing Versace gown, but we can’t! When Penelope Cruz showed up to the Academy Awards red carpet in 2007, wearing this masterpiece and tribute to all that is glam, we fell to our knees. No, really.
Stylist Estee Stanley recalls this moment as one of the proudest in her entire professional life. From the detail on the bodice to the bold skirt and train, this is truly an iconic fashion moment that we’ll remember forever.
10 Nicole Kidman In 2007
Wearing a brilliant red dress can either turn you into a style sensation overnight or can get you landed on every worst-dressed list around the world. Luckily, Nicole Kidman pulled off this Balenciaga gown at the Academy Awards in 2007.
Our favorite element to this look is that the train starts at the neck, plus the bow saves it from being just another red dress. While the bow may have been too much for a less confident actress, the tall and graceful Kidman holds her own in the dress.
9 Reese Witherspoon In 2007
Reese Witherspoon gets her fashion right so often that she’s probably one of our most highly anticipated red carpet walkers. This Nina Ricci gown that she wore to the Golden Globe Awards in 2007 was no exception.
Some fashion critics even labelled it as her “comeback” dress. The red shoes were a bold move, but we think they enhance the deep yellow of the dress, which is perfectly complemented by the actress’s blonde locks. She was a vision in gold at the Golden Globes!
8 Sienna Miller In 2007
With the metallic detail on the front of Sienna Miller’s white gown, you’d be forgiven for thinking that she was a Greek goddess who’d fallen from Olympus. The actress wore this Marchesa dress to the Golden Globes in 2007, and, with that extravagant train, conjured images of all that is holy, along with mythology, royalty, and bridal fashion.
This was definitely a big look to rock, but Miller did. The milkmaid’s braid brought about a more relaxed vibe, which totally worked.
7 Beyonce In 2008
In terms of red carpet expectations, the Grammys aren’t like the Academy Awards or the Golden Globes. You can run into anything on the Grammy red carpet, but Beyoncé did not disappoint in 2008, when she was the awards paying tribute to her idol Tina Turner.
This Elie Saab gown with silver sequins and lots of tulle was fit for a queen like Beyoncé and was fun and bouncy just like her lob. More than ten years ago, this was around the time B married long-time boyfriend Jay-Z.
6 America Ferrera In 2008
Gray isn’t the most common color to see on the red carpet, but we love it on America Ferrera. Here she is in her charcoal gray gown by Monique Lhullier at the Screen Actors Guild Awards in 2008.
The Ugly Betty star was a nominee for Best Actress in a Comedy Series that night, but there was nothing funny about this elegant lace piece, complete with a jeweled shoulder for extra oomph. Ferrera opted for Jimmy Choo heels to wear with her spectacular dress.
5 Anne Hathaway In 2009
Anne Hathaway did not disappoint at the Academy Awards in 2009. This Armani Prive gown was simply exquisite, channeling a very glam mermaid. This fashion moment is iconic because it helped Hathaway step out of her former teen-star self and earn recognition as a grown-up serious actress (with impeccable style).
There is nothing we would change about this dress, and it didn't need a necklace to turn up the sophistication factor. Hathaway was beaming in it and looked the best we’d ever seen her.
4 Eva Mendes In 2009
Stars have to be careful with all-white gowns on the red carpet, but Eva Mendes took a risk with this splash of turquoise, and it served her well. She wore this Christian Dior dress to the Golden Globe Awards in 2009, and it was so well-received that her stylist, Rachel Zoe, received acclaim and recognition for thinking to match up the white and turquoise.
The necklace makes the dress that little bit more fun and certifies it as an iconic fashion moment.
3 Penelope Cruz In 2009
At the Academy Awards in 2009, while some stars opted to have more fun on the red carpet, others went all out for that glamorous, almost princess-like look. Penelope Cruz strayed away from minimal and simple and instead went for this extravagant vintage ball gown by Pierre Balmain.
There’s only one thing that could make the dress worthier of a fairy tale, and that’s the golden Oscar sitting firmly in the actress’s hands. Magic was certainly in the sky that night!
2 Olivia Wilde In 2009
It was surprising to see Olivia Wilde in this lavender gown in the January of 2009, when she stepped out onto the red carpet at the Golden Globe Awards, but we think the color is what makes this dress stand out from all the other fabulous fashion that night.
The actress dazzled in this Reem Acra gown, which fit her perfectly. Commentators were pretty united when it came to this look: it’s definitely a keeper, and one of Wilde’s best.
1 Drew Barrymore In 2009
Another star who turned heads at the Golden Globes in 2009 was Drew Barrymore, who stunned in this gown by John Galliano. The fashion critics at Entertainment Weekly called this asymmetric gown one of their best looks of the night, although they thought that the actress needed to “turn down the volume on her hair—by a few notches—to make this an all-out best.”
Barrymore matched up the gown with a red clutch by Roger Vivier and definitely made waves in more ways than one!
Sources: Entertainment Weekly, Vogue, Harpers Bazaar, Style Caster