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Headbands have come back in style numerous times over the years, including in the early 2000s with the popularity of teen drama "Gossip Girl," on which the main characters wore them almost constantly
Meg Ryan Meg Ryan in this coat the "Anastasia" New York City premiere in 1997
Big Ol' Baggy Jeans Pooling, wide-leg jeansthe kind gloriously offbeat dressers like Justin Bieber and Pete Davidson swear by todayremain a calling card of Y2K-era fashion, but the cut first took off in the decade that preceded it
In 1991, Madonna and Michael Jackson arrived to the 63rd Annual Academy Awards in the most glamorous Hollywood outfits
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