39. Madonna’s Decked Out Jewels
Designer: Harry Winston
Event: 1991 Oscars
Worth: $20 million*
Demure and subtle are usually not words that you use to describe pop star Madonna. However, the singer tried out a traditional look at the 1991 Oscars, and it was a smash-hit. Madonna borrowed millions of dollars’ worth of jewels from Harry Winston to complete her look, which included a white, strapless dress, fur stole, and curly, Marilyn-Monroe-esque blonde hair.
Madonna’s Decked Out Jewels @GroovyDaij / Twitter.com
One of the main pieces that Madonna wore was the diamond cluster necklace, which would later become iconic. Winston came up with the design in the 1940s after he was inspired by Christmas decorations outside of his Scarsdale, New York home. He said that he wanted to make a holiday wreath, but, instead of “green needles,” there would be “diamonds.”