’90s Celebrity Fashion Flashback!

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Madonna

Madge donned her infamous cone bra during 1990's "Blonde Amibition" world concert tour.

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*NSYNC

Their music topped the charts in the '90s but Justin Timberlake, Lance Bass, Chris Kirkpatrick, J.C. Chasez and Joey Fatone made a major fashion fail posing on the red carpet.

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Angelina Jolie

Nice shoulder pads, Angie! Jolie sported an oversized lavender business suit for the premiere of Tru in 1991 alongside her dad Jon Voight.

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Kim, Khloe, Kourtney and Rob Kardashian

Years before they became household names, the blended Kardashian-Jenner family -- including Brandon and Brody Jenner -- was just another brood who dressed in matching outfits for annual portraits. The look for 1991? Denim on denim.

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Brad Pitt and Julianne Lewis

What would Angelina Jolie say about this look?! Pitt and his then-girlfriend Juliette Lewis stepped out on the red carpet at L.A.'s Last of the Mohicans premiere in 1992.

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Tom Cruise and Nicole Kidman

Kidman sported a printed frock and matching sunhat to support then-husband Cruise when he immortalized his hand and footprints at L.A.'s Grauman's Chinese Theater in 1993.

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Ryan Seacrest

Long before his American Idol hosting stint began, Seacrest (here in 1994) was a stylin' radio DJ in his hometown of Atlanta.

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Katherine Heigl

The future Knocked Up actress chose a monochromatic ensemble to attend 1994's City Slickers II premiere in New York with her mother Nancy.

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Jennifer Lopez and Wesley Snipes

Lopez topped her floral dress with a fur-trimmed coat to attend Elton John's 1995 AIDS Foundation Gala with Snipes.

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Will and Jada Pinkett Smith

Blue was the color of choice for Jada when she and her then-boyfriend attended 1995's Devil in a Blue Dress premiere in Beverly Hills.

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Mariah Carey

Carey -- then wed to Tommy Mottola -- chose a slinky red spaghetti strap gown for an event at which she posed with a decidedly less formally dressed Rosie O'Donnell in 1996.

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Gwen Stefani

Nothing says the Grammys like outlandish fashions and No Doubt singer Stefani's 1997 mixed print ensemble -- note the leopard lining of her floral coat -- is one look that definitely turned heads that year.

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Ben Affleck and Matt Damon

Damon and Affleck came together at Good Will Hunting's 1997 premiere.

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Lindsay Lohan

Long before she stripped down for Playboy, Lohan was a demure child star (dressed age-appropriately!) at the 1998 world premiere of her film The Parent Trap.

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Beyonce

1998 was the year of the midriff for Kelly Rowland (left), Beyonce (second from left) and their Destiny's Child band mates LaToya Luckett and LaTavia Robertson, who posed together at the Soul Train Awards in all-black ensembles.

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TLC

Tionne "T-Boz" Watkins, Lisa "Left Eye" Lopes and Rozonda "Chilli" Thomas spelled out their group's name on their wardrobe at the 1999 Nickelodeon Kids Choice Awards. Group member Lopes passed away in 2002 and her band mates continued to release music as a duo.

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Christina Aguilera

The "Genie in a Bottle" singer showed off her whittled middle in a black mesh skirt and colorful knit shawl at 1999's 1st annual Teen Choice Awards.

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Britney Spears

Playing off MTV's signature silver Moonman trophy, Spears wore a metallic hue from head-to-toe when attending the 1999 MTV Video Music Awards.

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Jennifer Aniston

Jen at the Emmys! In 1999, the actress -- attending on the arm of then-boyfriend Brad Pitt -- donned a brown beaded Randolph Duke dress.

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Jessica Alba

Alba went casual for 1999's Big Daddy premiere in cuffed jeans, a purple camisole and sweater and stripy heels.