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1999: Emmy Awards Everything about this photo screams Y2K, from Pitts hair and sunglasses, to Anistons own do, and of course, theres the actors Randolph Duke dress featuring an embellished top and brown column skirt

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SHOP PLAID SKIRT Horizontal-Striped Shirts NBC Images Neon-colored striped shirts, like this green and yellow mix worn by The Fresh Prince of Bel-Air star Will Smith, were a popular street style look