Here Are 20 Of The Most Iconic Red Carpet Looks From 2000

Award season is one of our favourite times of the year because we get to see what amazing outfits the celebrities are going to grace us with. Some of them choose creative dresses, like Lady Gaga, while others will choose elegant works of art, like Blake Lively. We always look forward to what they are going to present us with every year.

As award season is upon us, we thought we would take a trip down memory lane and see what was on the red carpet during the year 2000. Some you will remember because they were iconic and others will make you wish the style would come back again. Either way, you will have fun looking through them again.

20 Britney Spears At The Grammy Awards

via Business Insider

Britney Spears was at the top of her game in 2000 and dating the handsome Justin Timberlake. If she could look back on things then, we wonder what she would do differently. She looked elegant at the Grammy Awards that year, wearing an elegant white dress that looked beautiful against her honey-blonde hair. It was clear that Britney wasn't only inspiring fans with her music but her fashion choices, too!

19 Nicole Kidman Is The Golden Girl

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Nicole impressed everyone at the 2000 Oscars with this mesmerizing gilded gown. It practically made her glow. At the time, Kidman was still married to Tom Cruise. She might look stunning standing there in the dress, but she has stated it’s not her favourite thing to do.

“I find standing and posing for photos very awkward,” she said, as Indian Express reports.

Could've fooled us! She looks like a natural.

18 Penelope Cruz Impressed At The Grammys

via E! Online

We don’t see as much of Penelope Cruz these days as we would like to. In the year 2000, she headed to the Grammy’s looking sleek in a suit. One of the best parts of walking the red carpet has to be the fact that you get to wear amazing designer clothes.

“There are so many designers that I love, and I'm so lucky that I get to work with so many of them and sometimes spend time with them,” the actress has said, as Female First reports.

17 Cate Blanchett At The Oscars

via Glamour

Cate Blanchette is always a class act and she was an eye-catcher at the Oscars that year. We love the black backless Jean Paul Gaultier dress she wore. She looks just as good as she ever did - she never seems to age.

“A lot of people are frightened by old age — by being around people who are, basically, on their way out — but I'm fascinated by it,”

she said, as The Daily Mail reports. “It's an amazing thing to be around someone who has had a life well lived.”

16 Faith Hill Showed Us Shrugs

via E! News

Do you remember when shrugs were a thing? They covered just the top of your shoulders so that you could be warm without hiding your dress too much. Faith Hill brought the shrug to the Grammys that year.

What's so great about her is that she's gorgeous and fashionable but doesn't define herself according to those characteristics.

“I think beauty comes from within. If you're happy and look at life in the best way you can, even when there are problems, it can make you beautiful on the outside,”

Faith has said, as Medium reports. Well said!

15 Angelina Jolie Had The Goth Vibe

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This was the time when Angelina Jolie was into the dark vampire look. She had super-long black hair and wore a black dress to the Oscars. She was clearly dressed for success as she won an Oscar for Best Supporting Actress in the movie, Girl Interrupted. Her goth vibe was certainly memorable - this is still one of her most intriguing looks ever.

14 NSYNC Was Not In Sync

via E! News

One memorable red carpet moment was when the band 'N Sync showed up to the Grammys looking like they had purchased outfits from a flea market. They are so bad that it’s hard to believe that this is a popular band at a fancy event. They would have done better to get matching attire instead of whatever happened here. There was a lot of fashion missteps in the year 2000 and these guys will go down in history with these outfits. No wonder the band broke up.

13 Hilary Swank Surprised Us In Green

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Another Oscar winner in 2000 was Hilary Swank and she looked amazing in a green ballgown. She won Best Actress for her role in the movie Boys Don’t Cry. As Successories states, she said about the role,

“The truth is, after Boys Don't Cry, I realized how few and far between the great roles are. I am beyond thankful for finding Million Dollar Baby.”

We haven’t seen Hilary Swank for a while in Hollywood, so it’s nice to look back at the amazing style that she rocked and this one was certainly a winner for her.

12 Christina Aguilera Blinded Us

via E! News

This Grammy look wasn’t Christina Aguilera’s best, but this was back in her younger days when some would say she could have used a stylist. But the reasons why her look is so memorable here and deserves a spot on this list is because it captures a youthful and fun attitude. Plus, we're loving the slight mermaid sheer of her silver dress and the playful shoes she was bold enough to add to her outfit.

11 Leelee Sobieski Turned Heads In This Sky-Inspired Dress

via Wetpaint

Okay, reality check: she actually made people shudder when she showed up in this multi-coloured dress. We have to give her credit for trying but she is young and it wouldn’t be the first time that a young celebrity got it wrong on the red carpet. What are those designs on the dress lining, flowers or bats? Either way, maybe this dress was a little too OTT to be stylish. That said, it's certainly memorable!

10 Halle Berry Shines In Red And White

via Galore

Halle Berry definitely caught everyone’s eye when she wore this gorgeous red and white Valentino gown. She also won a Golden Globe that year for Best actress in a TV movie. It doesn’t seem to matter what she wears, she always looks incredible, so it's no surprise that she modelled before becoming an actress.

“I never wanted to be a model. My modelling career was nothing but a stepping stone to my acting career and that's all I ever saw it as,” Halle says, as The Richest reports. “A pointless rock in the river that has to be stepped on in order to get to the meaningful oasis of acting.”

9 Cher Is Timeless In Classic Black

via Harper's Bazaar

We love how amazing Cher looks in this black gown. She always seems to get things right when it comes to fashion, even when she tries something different. Someone could easily wear this beautiful outfit to an awards event now and still rock the look because it's so timeless. The gown's diamond straps and off-the-shoulder style are still considered trendy today. Much like her looks, it seems Cher's style never ages.

8 Laura Dern Sparkled At The Golden Globes

via Us Weekly

This is a blast from the past and we almost forgot that Laura Dern and Billy Bob Thornton were a couple. They were actually engaged at one time until he met Angelina Jolie. Laura did look lovely that night in a dress that was elegant while still having all the sparkle you could ask for when dressing up for a big night. It suited her skin tone and hair colour perfectly.

7 Denise Richards Made A Poor Choice

via Harper's Bazaar

We’ve never understood why some celebrities will wear jeans or pants to a red carpet event. It’s like they didn’t care enough to put any effort into their outfit. In this case, however, Denise rocked the look. A bit of shimmer in her corset gives her casual look an edge, while the gold and white of her outfit creates a glamorous appearance. We especially love her volume-packed curly hair!

6 Jennifer Lopez Thought She Was Going To Prom

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Prom style — that’s the only way to explain this fuchsia dress that Jennifer wore to the 2000 Alma Awards. The colour looks beautiful on her and the halter-neck style really seems to add elegance to the dress. She nailed the pose! Although it might feel a bit dated to wear this now, there's no doubt that this dress forms part of JLo's many gorgeous outfits over the years. She's definitely a style icon.

5 Sarah Jessica Parker Wore Vintage

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Sarah Jessica Parker looked incredible in a Richard Tyler gown for the 2000 Golden Globes. It’s one of the best outfits of the year. She’s also an actress that designers love so she usually gets to wear some pretty nice things.

“When I go to a premiere, I like to borrow lovely clothes and shoes from designers,”

she said, as IMDb reports. “It's like the library: if you return them in good condition, you get to borrow more. I'm very lucky.”

4 Gwyneth Paltrow Goes Dark

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When Gwyneth wore chic black-and-white at the 1996 Golden Globes, she made it onto the best-dressed list, as W magazine reports. Cut to 2000, and it seems she lost her way a little, style-wise. Maybe she just wanted to feel comfortable or maybe she had a business meeting to go to after, we’re not sure, but this is one of the most underwhelming Golden Globes outfits that we have ever seen.

3 Courtney Love Wore A Ripped Garbage Bag

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That’s what it looked like anyway. She made headlines that year for basically wearing the worst dress ever to the Golden Globes in 2000. We can’t imagine what she was thinking putting on this tattered dress. But, in true Love style, she doesn't care what people think. As International Business Times reports, she's said about fame,

“Being famous is just like being in high school. But I'm not interested in being the cheerleader.

I'm not interested in being Gwen Stefani. She's the cheerleader, and I'm out in the smoker shed.”

2 Cameron Diaz Wore A Curtain

via Cosmopolitan

Cameron Diaz was highly successful at this point so we wonder why she didn’t make better fashion choices when it came to hitting the red carpet. She's such a gorgeous woman that she would have looked incredible in an elegant dress. Instead, she chose something that looked like a curtain. It also fitted her in a weird way. Instead of accentuating her figure, it made her look like she was wearing a sack!

1 Julia Roberts Was Underwhelming

via The Telegraph

With all the elegant dresses that have hit the red carpet, we were surprised when Julia showed up at the Golden Globes looking like she was just going to a backyard BBQ. This look is especially surprising considering she loves fashion so much. As she told W magazine,

“I did get to keep the wedding dresses from Runaway Bride. They're all boxed up in my garage. I've never opened them.

It'll be fun one day when [her daughter] Hazel is taller. She can play dress-up with her friends.”

References: The Daily Mail, NY Daily, IMDB, The Richest, W Magazine

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