The 13 Most Expensive Pieces of Celebrity Jewelry Art Celebrity Jewelry - Angelina Jolie phillyfashionistas.com $2.5 million This list comprises the most expensive pieces of celebrity jewelry ever worn. Angelina Jolie is one of the most beautiful women in the world. So it’s no surprise that her jewelry is also beautiful. Angelina Jolie showed up at the 2009 Oscars wearing an astonishing pair of earrings. The emerald drops cost an absolutely staggering two and a half million dollars. The earrings are now famous as one of her best-ever looks. The earrings were designed by Lorraine Schwartz. They were dazzlingly beautiful. The emeralds were 115-carat.