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LEIGHTON MEESTER: 2009
The gold standard by which all other Teen Choice Awards looks are measured: adorable striped Louis Vuitton number and totally on-point ruby slippers. It was both so Blair Waldorf and totally timeless (for the TCAs, anyway) at the same time.
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NICOLE RICHIE: 2004
was starting to transition from her role as Hollywood party girl and into a Simple Life-fueled star in her own right. She celebrated by picking this floaty beige slip dress that she’d absolutely wear today (though with completely different accessories).
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JESSICA SIMPSON: 2006
The got it so right on the red carpet in this cute low-necked pastel yellow party dress … which is why we were floored when she got it so, so wrong onstage that year.
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ALEXIS BLEDEL: 2005
Mentally incinerate those blah bow-topped kitten heels, then admit it – you’d totally wear the Gilmore Girls star’s dress to a summer wedding, wouldn’t you?
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Perhaps the most surprising thing about this photo is that style has become harder to emulate as the years have gone on.
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LAUREN CONRAD, 2008
There isn’t much left “Unwritten” about style, so we’ll just say this: We loved her beach-babe Hills red carpet vibe back then, and we love it just as much today.
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MILA KUNIS: 1999
If you’ve been resisting the ’90s trend resurgence, we kinda feel like this very wearable, understated look may be the thing that convinces you to give in to it.
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MISCHA BARTON: 2006
At the height of her O.C. powers, Mischa killed it on the red carpet wearing a dress that would look just as cute on any TV “It Girl” today.
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JENNA DEWAN-TATUM: 2006
Before she added the “Tatum” (and well before she embraced her natural skin and hair tones), the Step Up star stepped out in a flowy, retro-inspired powder pink halter with contrasting hot pink sandals.
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SARAH MICHELLE GELLAR: 2001
We’re not necessarily saying we’d wear this exact outfit today, but we’ve definitely seen all these components on different celebrities within the past month. And hey: She looks cute!