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Some historical figures are inseparable from the clothing they wore, like Audrey Hepburn in her little black dress or Judy Garland in a blue-checked pinafore. And in recent years, auction houses have made headlines as they’ve sold these iconic pieces for sky-high prices – with Julien’s Auctions setting the Guinness World Record for the most expensive dress ever sold at auction in 2016. After being purchased at auction, famed dresses can take on a second life – often preserved in private collections but sometimes appearing back on the red carpet.

Read on to learn more about some of the most expensive dresses ever sold at auction. 2 / 7 Dorothy’s black & white gingham dress: $750,000 Dorothy’s black & white gingham dress: $750,000 There are an estimated five surviving Dorothy dresses that have moved through private collections since the premiered in 1939. In 2019, Heritage Auctions sold a black and white variant of the gingham dress for $750,000.



The black and white dress is notable for being the only Dorothy dress that can be linked to specific scenes in the film. When Dorothy steps out of black-and-white Kansas and into technicolor Oz, Judy Garland’s body double Barbara Koshay can be seen wearing the dress. By rendering the normally blue dress in black the filmmakers were able to more smoothly show the transition between Kansas and Oz – with the scene quickly transitioning from Koshay in black to Garland in blue.

3 / 7 Audrey Hepburn’s “Breakfast at Tiffan.

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