19 Red Carpet Photos That Perfectly Display How Crazy The Early 2000s Were

Early 2000s fashion was mostly iconic, but sometimes bizarre.

Fashion in the early 2000s is arguably one of the most eclectic times in style history.

Those who are old enough to remember or participate in the trends that emerged in the early 2000s can recall how outrageous some of them were. While some of us may have lived for the dress-over-jeans look back in the mid-2000s, many would cringe at the thought of wearing that type of outfit nowadays.

Albeit there were many Y2K-era fashion hits, there were also many fashion faux pas that derived from the early 2000s. The few opening years for the new millennium were somewhat of a perplexing time, and these 19 celebrity red carpet photos summarize just how bewildering some of the 2000s fashion looks were.

1. Britney Spears & Justin Timberlake

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Britney Spears and Justin Timberlake made fashion history with their denim-on-denim look for the 2001 American Music Awards. The early 2000s red carpet looks were never the same after that. 

2. Sisqó

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Everything about Sisqó was extra during his mainstream R&B reign between 1999–2000, and fans were here for it. When it came to Sisqó in the late '90s and early 2000s, he made it his mission to be the most standout artist in his generation, hence his platinum silver blonde hair and dynamic outfits. It most definitely worked because he ended up being a major superstar at the start of the millennium. 

3. Pink

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Pink, before she became a punk rocker and still was an R&B songbird, had an eccentric urban street style that was accentuated by her hot pink short haircut. Her red carpet appearance at the 2000 MTV Video Music Awards was definitely a sight to see then, and now. 

4. Ashley Tisdale

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Ashley Tisdale embodies mid-2000s fashion. Each time Ashley Tisdale was on the Disney red carpet, she was practically a walking billboard for the latest trend of that time period.

5. Ashley Tisdale

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This is Ashley Tisdale on the red carpet for the 2004 The Incredibles premiere. I rest my case. 

6. Christina Aguilera

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Early 2000s Christina Aguilera was always good for an extreme hip high split and deep cleavage cut top. The 2000s time was truly a "your body is the fashion" type era, and Aguilera showcased that at the VH1 Music Awards in 2000.

7. Paris Hilton

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No one dressed quite like how Paris Hilton did in the 2000s.

8. Rihanna

John Sciulli

Rihanna definitely had a certain look when she first stepped on the scene in the mid-2000s. RiRi's style has evolved significantly since 2005 obviously. 

9. Pamela Anderson

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Crinkled hair and feathered dresses was a signature style in the early 2000s, as modeled by Pamela Anderson arriving at the World Music Awards.

10. NSYNC

Steve Granitz / WireImage

2000s NSYNC epitomizes everything that Y2K was.

11. Jennifer Lopez

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Jennifer Lopez rarely ever is a fashion no-no — however, this red carpet look for the 2001 MTV Music Awards might be a fashion maybe. 

12. Lil Kim

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Lil Kim has always been a risk taker and trendsetter when it cam to hip-hop fashion, and her red carpet appearance at the 2001 Source Hip-Hop Music Awards is evident of that. 

13. Destiny's Child (when they were D3)

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Some of Destiny's Child's looks, specifically when they went from D4 to D3, were a bit interesting...

14. Mischa Barton

Tsuni / USA / Alamy Stock Photo

I still wonder why so many of us were obsessed with wearing formal dresses over jeans like Mischa Barton did at the 2004 Nickelodeon Awards.

15. Avril Lavigne & Kelly Osbourne

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Early 2000s emos and punks alike dressed almost identically to how Avril Lavigne and Kelly Osbourne did on the 2003 MTV Video Music Awards red carpet.

16. Hilary Duff

Featureflash Archive / Alamy Stock Photo

Do you ever wonder if Hilary Duff thinks back to the outfit she wore on the orange carpet for the 2003 Nickelodeon Kids' Choice Awards and goes, why did I wear that? Or is it just me?

17. Gwen Stefani (during her Harajuku era)

Tsuni / USA / Alamy Stock Photo

Gwen Stefani's stylish yet culturally appropriating Harajuku fashion phase was definitely a wild time. Although Stefani using the Japanese subculture for her creative expression was problematic, it must be admitted that this era of Stefani was eye-grabbing. Whenever Stefani stepped on a red carpet with the Harajuku girls, like she did at the 2004 American Music Awards, it always captivated you, whether that was for a good or bad reason.

18. Eve

George De Sota / Getty Images

Rapper Eve most of the time slayed on the red carpet in the 2000s, but this look on the 2000 MTV Video Music Awards wasn't up to par with her later red carpet outfits.

19. Nicole Kidman

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I really would like to have a sit-down discussion with Nicole Kidman about why she chose this particular red carpet look for the 2003 UK Royal Charity Premiere of Cold Mountain.

What other celebrity red carpet looks showcase how wild the 2000s was?