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Think of Jennifer Lopez’s fashion moments, and what’s the first thing that comes to mind? Probably the plunging, green Versace dress that she wore to the 2000 Grammy Awards. It might be her most memorable look, but it was at various MTV Video Music Awards shows over the years where J. Lo appeared to feel her freest in terms of experimentation. At the VMAs — where red carpet rules are bent and celebs sport wilder clothing — she could don leopard print, Space Age minidresses or a handkerchief hemline if she so chose. The result: some of her most iconic outfits and beauty concepts.

Ahead of her Michael Jackson Video Vanguard Award, which she will receive during this year’s VMAs on Monday, Aug. 20, we’ve culled her best and most nostalgic looks — including those from the days on Diddy’s arm.

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