This Is What Anna Wintour Wore to the Met Gala Nearly 30 Years Ago

Gina Marinelli

The Costume Institute at The Metropolitan Museum of Art’s annual gala benefit, or more commonly known as the Met Gala, is not just the most extravagant and exclusive fashion event of the year; it’s the work of Anna Wintour. While the biggest role on her résumé may read editor in chief of Vogue, Wintour first hosted the Gala back in 1995. And later in 2014, after helping secure approximately $125 million for the institution, The Met named the wing after her, now known as the Anna Wintour Costume Center. So what does the Met Gala’s biggest fan and supporter wear? Well, it’s changed over the last 30 years. A lot.

In preparation for Monday’s red carpet, we tracked down some of the very best Wintour looks from galas past, all the way to 1988, the year she took the helm at Vogue in the U.S. And naturally, we caught on to a few themes. Firstly, Wintour’s looks always have a subtle nod to the theme but never quite border on “costume”-y; she has a penchant for fuzzy statement accents; and when it comes to designers, there’s one that usually weighs out all others. You won’t be able to miss it.

Take a look at a bit of fashion history ahead, and see some of the best Met Gala looks from its most devoted attendee.

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