New York Fashion Week in the 2000s: Celebrity photos fashion flashback

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With New York Fashion Week in full swing — it runs from Sept. 9 to Sept. 14, 2022 — Wonderwall.com is taking a stroll down memory lane to reminisce about what NYFW looked like back in the 2000s. Curious to see which stars were on hand for the biggest shows? Let’s get started with a quintessentially 2006 photo of Lauren Conrad, Heidi Montag and Ryan Cabrera! The “The Hills” frenemies and the pop star posed for this awesomely aughts snap at the Yellow Fever & Clandestine Industries Spring 2007 fashion show in September that year.

Keep reading for more amazing throwback photos…

RELATED: Celebrity couples who dress alike

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Lonely Boy and… Taylor Swift? Think of the songs this relationship could have inspired! Unfortunately, “You” hunk Penn Badgley and then-country singer Taylor were never an aughts item. They did, however, sit next to each other at the Tommy Hilfiger Spring 2010 show in September 2009.

RELATED: The biggest celebrity summer trends from the early 2000s

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Aughts icons! Hilary Duff and Amanda Bynes attended another a show by another ’00s staple — Herve Leger — during New York Fashion Week in 2009.

RELATED: Heidi Klum’s wildest and sexiest fashion moments

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Back when Beyonce was still among the “Single Ladies,” she and a young JAY-Z sat front row at the Rosa Cha show during New York Fashion Week in September 2003.

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Name a more random duo! We’ll wait… (Yes, that’s David Copperfield and Serena Williams sitting together at the Y And Kei Spring 2005 show in September 2004.)

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Felicity, the girl from the Doritos commercials, and the little girl from “The Horse Whisperer” is probably how someone in 2002 would have described who’s in this photo! The ladies — Keri Russell, Ali Landry and Scarlett Johansson — took in the BCBG Max Azria show during New York Fashion Week that September.

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We’re sensing a duet we would have loved! Carrie Underwood and Eve both showed up for Gwen Stefani’s L.A.M.B. Spring 2008 show during New York Fashion Week in September 2007. Unfortunately for us, this didn’t result in a musical collaboration.

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Anne Hathaway and Jessica Simpson couldn’t contain their excitement while in attendance at the Luca Luca Couture Spring 2005 fashion show in September 2004.

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When you think New York Fashion Week, you definitely think Clay Aiken, right? Surprise! Back in September 2005, the “American Idol” runner-up attended the Kenneth Cole Spring 2006 show seated right next to country crooner Lee Ann Womack.

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Here’s an odd duo! Diddy, who went by Sean “P. Diddy” Combs in those days, palled around with boybander Nick Lachey at the Tommy Hilfiger fashion show in September 2004.

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Mary-Kate Olsen and Ashley Olsen wearing color? Yep, back in 2004, the two made public appearances often, including this stop at the Marc Jacobs show during New York Fashion Week that September.

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Spotted: Serena van der Woodsen! During the “Gossip Girl” era, Blake Lively sat front and center at the Miss Sixty Spring 2009 show… right next to Rosario Dawson. The two were photographed during New York Fashion Week in September 2008.

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LeAnn Rimes, Dean Sheremet and… Zooey Deschanel? Before LeAnn and hubby Dean split, they once shared the front-row spotlight with the future “New Girl” star at the Marc Jacobs Spring 2007 fashion show in September 2006.

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Gabrielle Union, Kim Kardashian, Ciara and Kelly Rowland sat together in the front row during the Tracy Reese Spring 2010 fashion show in September 2009.

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Who knew Natalie Portman and Mandy Moore were such good friends? Both famous ladies were on hand for the Marc Jacobs show during New York Fashion Week in September 2004.

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Way before she joined the cast of “The Real Housewives of Beverly Hills,” Tinsley Mortimer was known for being a New York socialite. She made the rounds at Fashion Week in September 2005 and posed alongside fellow party girls Paris Hilton and Nicky Hilton at the Alvin Valley Spring 2006 fashion show.

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Friendly exes? JC Chasez and Tara Reid attended the Custo Barcelona Spring 2006 fashion show in September 2005… three years after they were rumored to have been an item.

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Rashida Jones and Nicky Hilton had a laugh while waiting for the Charlotte Ronson Spring 2007 fashion show to start during New York Fashion Week in September 2006.

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A year after they tied the knot, Sarah Michelle Gellar sat on Freddie Prinze Jr.’s lap at the Tommy Hilfiger fashion show in September 2003.

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Future “Weeds” star Mary Louise Parker caught a show next to “The O.C.” star Mischa Barton! The two were photographed at the Luca Luca Couture Spring 2005 fashion show in September 2004.

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The way they were! Exes Josh Duhamel and Fergie were ready for the Tommy Hilfiger Spring 2006 fashion show in September 2005 — four years before they tied the knot.

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Here’s a throwback snap! Mary J. Blige and Janet Jackson checked out the fashions at the Baby Phat show together back in September 2004.

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Check out this pairing! LL Cool J and Jimmy Fallon were seated together during the John Varvatos show in September 2005.

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Carmen Electra and Mexican superstar Thalia posed for photos from the front row of the Luca Luca Spring 2007 show during New York Fashion Week in September 2006.

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Long before Kim Kardashian became Kim Kardashian West, Kanye West attended fashion week with then-fiancée Alexis Phifer. The two posed in the front row at the Luca Luca Spring 2007 show in September 2006.

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Anna Kournikova and Jamie-Lynn Sigler (who went by her then-married name, Jamie-Lynn DiScala) matched in black at the Monique Lhuillier Spring 2006 fashion show in September 2005.

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So yesterday! Hilary Duff posed with Maria Menounos and Usher at the Michael Kors Spring 2007 fashion show in September 2006.

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Just a few months after they tied the knot, Marc Anthony and Jennifer Lopez sat front row at Marc Jacobs’ Spring 2005 fashion show in September 2004.

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Two of the biggest reality stars in the aughts? Paris Hilton and Kelly Osbourne! The ladies caught the Kai Milla Spring 2006 fashion show together in September 2005.

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January Jones and Kelly Rowland posed for photos in the front row of the BCBG Max Azria Spring 2007 show in September 2006.

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What do you suppose Mandy Moore, Ashley Olsen and Eva Mendes talked about while sitting front row at the Oscar De La Renta Spring 2005 fashion show? We may never know, but at least they agreed to pose for photos during New York Fashion Week in September 2004.

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Check out Nicole Richie and Gwen Stefani posing together over a decade ago! The two were both on hand for the “Fashion For Relief” show in September 2005.

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Here’s a very mid-’00s snap! A “Grey’s Anatomy” era Katherine Heigl, Jesse Metcalfe and Sophia Bush nabbed prime real estate during the Tommy Hilfiger Spring 2006 fashion show in September 2005.

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Kerry Washington cracked up Elisabeth Hasselbeck before the Nanette Lepore Spring 2006 fashion show in September 2005.

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If only Venus Williams had been there it would have been a double-sisters outing! Nicky Hilton, Paris Hilton and Serena Williams all caught the Spring 2005 Tommy Hilfiger show together back in September 2004.

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“Newlyweds” stars Jessica Simpson and Nick Lachey attended the Tommy Hilfiger show back in September 2003. Their legendary MTV reality show had debuted earlier that summer.

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Jessica wasn’t the only Simpson frequenting New York Fashion Week in the ’00s! Ashlee Simpson and mom Tina Simpson took in a BCBG Max Azria show (while seated next to Ciara!) during New York Fashion Week 2007.

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Front row and center for the Marc Jacobs show in September 2003? Kelly Osbourne and Diddy, who went by Sean “P. Diddy” Combs back then.

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Then-married couple Demi Moore and Ashton Kutcher checked out the fashion at the Narciso Rodriguez Spring 2007 show in September 2006.

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Joy Bryant and Susan Sarandon were all smiles before the Donna Karan Spring 2006 fashion show in September 2005.

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Serena Williams, Hilary Swank and Elizabeth Hurley made a pretty odd trio at the Calvin Klein fashion show in September 2004.

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We forgot about this couple! Adam Goldberg and Christina Ricci, who dated from 2003 to 2007, took in the Rachel Comey fashion show in September 2004.

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Former BFFs Paris Hilton and Kim Kardashian watched the William Rast presentation in September 2006 accompanied by Kim’s then-boyfriend, Nick Cannon.

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Nick Cannon apparently loved to take girlfriends to New York Fashion Week! Back in September 2007, he took his then-main squeeze, model Selita Ebanks, to the Alexandre Herchcovitch Spring 2008 show.

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Anne Hathaway, Brandy, Venus Williams and Serena Williams all landed front-row seats for the Luca Luca Spring 2006 fashion show in September 2005.

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Emmy Rossum, Erika Christensen and Jaime King posed ahead of the Peter Som Spring 2007 show during New York Fashion Week in September 2006.

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Jason Lewis and Rosario Dawson were an item? The then-couple looked cozy at the BCBG Max Azria Spring 2006 show during New York Fashion Week in September 2005 in the middle of their two-year romance.

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Jessica Simpson and Eva Mendes sat side by side at the J. Mendel Spring 2005 fashion show during New York Fashion Week that year.

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Maggie Q shared a laugh with Andy Roddick at the Lacoste Spring 2006 show in September 2005.

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Hilary Swank and Demi Moore were an interesting pair at the Miss Sixty Spring 2008 fashion show back in September 2007.




















































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