Hilarious Times Celebrities Roasted Their Own ’90s and ’00s Fashion

Celeb '90s and '00s Fashion
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Photo: Allison Kahler/STYLECASTER/Getty Images

Depending on whom you talk to, the ’90s and ’00s were either the darkest or the greatest time in fashion. If you’re talking to us, the ’90s and ’00s were pretty snazzy. (Rachel Green and Cher Horowitz were fashion icons, and we’ll fight anyone who says otherwise.) But if you’re talking to ’00s-favorite celebrities such as Hilary Duff, Mandy Moore, and Ashley Tisdale, who came to the fame in these controversial fashion periods, you’ll probably hear a different answer.

MORE: 13 Actually Affordable Celebrity Outfits to Shop Immediately

We’ve rounded up the most hilarious times celebrities roasted their ’90s and ’00s fashion, from Tisdale’s keyboard purse to Moore’s plastic hair beads. The ’90s and ’00s were a fun time, but these celebrities aren’t looking back at their outfits fondly. When it comes to their style as teenagers, these stars don’t need you to remind them that they were a little out there—they already know.


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Ashley Tisdale

To the internet, no one is more '00s than Tisdale. The actress, known for Disney Channel's "The Suite Life of Zack & Cody" and "High School Musical," is known for her over-the-top '00s red-carpet looks, such as this one with a keyboard clutch, a skirt over jeans, and a T-shirt bedazzled with the word dream. Also, don't forget the time she wore a fur sash on a red carpet.

Ashley Tisdale
Mandy Moore

Moore, who rose to fame in the early '00s for her highly catchy pop song "Candy" and her career-making movie "A Walk to Remember," is known for poking fun at her past looks on Instagram. The singer-turned-actress had a wild time in the '90s and '00s, with looks from bucket hats and hair crystals to over-the-top spray tans—and she has pictures to prove it.

Mandy Moore
Mandy Moore
Brie Larson

Larson might not have had her big break until recently when she won an Oscar for her 2015 film "Room," but she had enough success in the '00s, with movies such as "13 Going on 30" and "Sleepover," to produce this red-carpet gem. At the 2004 Teen Choice Awards, Larson chose to wear a very Daphne Blake–esque hairdo and outfit complete with a plastic-looking skirt and oversized headband.

Hilary Duff

If you were raised in the '00s, you grew up watching Duff on "Lizzie McGuire." And though the actress might've been a teen idol, looking back, she wasn't exactly the most influential in the fashion department. Duff definitely has some memorable (and LOL-worthy) looks, from this red-carpet look with waxy pink pants and a patch-riddled denim jacket to the time she exposed her belly button in a robe at an awards show.

"I mean, I thought it was a fashion statement," Duff said of her robe look. "It was some kind of a statement. I'm not sure what kind."

Jennifer Love Hewitt

With iconic movies such as "I Know What You Did Last Summer," Hewitt was a scream queen in the late '90s. But to her, something scarier was her fashion. The actress shared this gem on Instagram with her sporting crazy-teased hair, a bedazzled tunic, and every bracelet she could find. (We also don't know what's going on with her sunglasses.) Hewitt is 11 in this picture, so it would've been taken in 1990, the beginning of her '90s fashion journey.

Busy Philipps

With cult-favorite '90s shows, such as "Freaks and Geeks" and "Dawson's Creek," Philipps influenced thousands of teens. But even she couldn't escape '90s fashion mishaps. This picture, taken when Philipps was a preteen, shows her and her friend in quintessential '90s gowns featuring huge, oversized sleeves, bedsheet-like patterns, and shiny satin. If you've watched any '90s movies or shows, you know that Philipps would fit right in with prom scenes.

Paris Hilton

Paris and her sister Nikki were It-girls in the '00s. Hilton was especially influential after her show "The Simple Life," with Nicole Richie, made it big. However, unlike other '00s mainstays, Hilton doesn't look back at the time in regret. In fact, she takes great pride in what she wore in the decade. We have to agree with her. Because this yellow and pink matching look that she and Nikki are wearing can only be described in one word: hot.

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  • Ashley Tisdale
  • Ashley Tisdale
  • Mandy Moore
  • Mandy Moore
  • Mandy Moore
  • Brie Larson
  • Hilary Duff
  • Jennifer Love Hewitt
  • Busy Philipps
  • Paris Hilton