In 2009, Madonna strutted in wearing thigh high boots and bunny ears.
And the following year the cameras were trained on tempestuous exes Jude Law and Sienna Miller then looking very much 'on'.
Dubbed the Oscars of the east coast, the Metropolitan Museum of Art's Costume Institute Gala has always been one of those gatherings that capture the imagination.
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This year's ball, hosted by the high priestess of fashion Anna Wintour, is bound to offer the usual mix of glamour, reverie, high culture and breathtaking frocks.
With the US Vogue editor's presiding, invitations to the New York soiree are more sought after than vintage Hermes bags, and the movie and catwalk gliteratti vy to take fashion honours.
On Monday, Anna will share hosting duties with British starlet Carey Mulligan and Italian designer Miuccia Prada.
The gala will celebrate Impossible Conversations – the museum's spring blockbuster exhibition exploring the striking parallels between Miuccia and her fellow countrywoman, the late Elsa Schiaparelli, a contemporary of Coco Chanel.
Meanwhile, Jennifer Lopez and funky newcomer Azealia Banks are rumoured to be performing.
As we eagerly anticipate the biggest event in the Big Apple's social calendar, here’s a look back at some of the best moments from past years.
Check back on Monday night for live updates from our Twitter account - @hellomagbeauty