Audrey Hepburn's Ascot Dress
This dress first appeared in My Fair Lady, released in 1964. Although traditional horse race fashion typically showcases cheaper, shorter skirt cuts, when Hepburn showed up in this Edwardian-style white lace dress, the image got burned into the minds of moviegoers everywhere.
Who, What, and How
Hepburn's dress was designed by a costume designer named Cecil Beaton. Beaton won an Oscar for best costume design for this dress alone. Sadly, neither Beaton nor Hepburn lived long enough to see this dress get auctioned off for $3.7 million in 2014.