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Brad Pitts Business Casual Brad Pitts ensemble at the Waterworld premiere in 1995 exemplifies the relaxed yet refined approach to business casual that defined 90s menswear

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

These dresses are more than just an outfit

So, with all that in mind, let's take a walk down memory lane, and revisit some of the weirdest and most generation-defining prom trends of the 2000s

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