1Keira Knightley and Rupert Friend (2006)
Getty Images 2Kate Bosworth (2004)
Getty ImagesMostly including this so that society never forgets low-rise trouser shorts were a thing we lived through.
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3Ashton Kutcher and Demi Moore (2007)
Getty ImagesJUST IN CASE you forgot that these two dated were married.
4Chris Martin and Gwyneth Paltrow (2005)
Getty ImagesTruly can't believe society endured an entire year of men wearing beanies like this.
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5Taylor Swift and Taylor Lautner (2009)
Getty ImagesNever forget that Taylor Swift's lyrics "You gave me roses and I left them there to die" are about this man.
6Drew Barrymore and Justin Long (2008)
Getty ImagesBefore he started a full-time job writing 40,000 word Instagram captions about his love for Kate Bosworth.
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7Julia Roberts (2002)
Getty ImagesOh this? Just the casual DIY shirt worn when her boyfriend Danny Moder's estranged wife Vera wouldn't grant him a divorce.
8Ben Affleck and Jennifer Lopez (2002)
Getty ImagesIf you were a celeb in the early 2000s and weren't photographed wearing a Juicy Couture velour tracksuit on some random balcony, not sure what you were doing.
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9Meg Ryan (2000)
Getty ImagesMeg Ryan just out here living life like it's an actual rom-com.
10Debi Mazar, Madonna, and Gwyneth Paltrow (2001)
Getty ImagesWILL NOT REST UNTIL SOMEONE EXPLAINS THIS FRIENDSHIP GROUP TO ME.
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11Katie Holmes and Chris Klein (2003)
Getty ImagesBootcut jeans. A wrinkled single-button blazer. That backwards newsboy cap. And a scarf I can only assume was stolen from my grandma's house.
It's all just working for me.
12Mariah Carey (2001)
Getty ImagesAs a card-carrying member of Mariah's Lambily, I'm going to need this belt.
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13Leonardo DiCaprio and Gisele Bündchen (2000)
Getty Images 14Elijah Wood (2002)
Getty Images"One does not simply walk into Mordor" *takes drag of cigarette*
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15Cher (2002)
Getty ImagesWow, so me-in-2024-coded.
16Kate Bosworth and Orlando Bloom (2005)
Getty ImagesChoosing to ignore his facial hair choices because this pap walk is everything.
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17Lindsay Lohan (2005)
Getty ImagesThis one really speaks for itself.
18Lenny Kravitz (2005)
Getty Images"I don't know a better person" — Oprah / me, looking at this photo
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19Ben Affleck and Gwyneth Paltrow (2002)
Getty ImagesUrgently need to know exactly what they were talking about.
20Victoria Beckham and Katie Holmes (2006)
Getty ImagesYou just don't get pics of celebs shoe shopping in public anymore, ya know?
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