90s Fashion Icons Princess Diana and Anna Wintour at Charity Gala (1996)

In September 1996, Princess Diana would collaborate with the Editor-in-Chief of Vogue, Anna Wintour, on a fashion benefit for breast cancer, through which the pair would become close friends for the remainder of Diana’s life. Wintour’s embrace of Diana further solidified the Princess of Wales’ role as an undisputed style icon of the the 1990s and America’s relationship with royalty in exile. Diana’s first and only appearance at the MET Gala just under two months later, remains a pivotal moment in MET Gala history.

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