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Designers like Calvin Klein, Helmut Lang, and Prada jumped on the momentum of a pendulum swinging away from the extreme opulence and exaggeration of 1980s fashion

Angelina Jolie Minutes after this photo was taken, Jolie jumped in the pool at the 1999 Golden Globes

Preppy fashion, you win again

Romeo + Juliet (1997) Baz Luhrmanns famed 1996 adaptation of the Shakespearean classic deserves a place on this list for many reasons

Mimi's glamorous bombshell style has continued to serve as style inspo for decades to come

The duo was often photographed on the red carpet in coordinating outfitsand for a short period, matching haircutsand their looks spanned the spectrum of '90s trends, from stark minimalism to grunge to preppy chic

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