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Going once, going twice, sold

Discover the most iconic pieces of pop culture which have fetched unbelievable amounts at auctions


Some collect coins, others collect stamps, while a rare few collect the most iconic pieces of pop culture. From Marilyn Monroe's 'Happy Birthday, Mr. President' dress, which made waves once again after Kim Kardashian wore it to the 2022 MET Gala, to Princess Diana's 'Travolta' dress, we've highlighted some of the most iconic items in the history of fashion that have fetched the most outrageous amounts of money at auctions.


Marilyn Monroe’s ‘Happy Birthday’ dress

It was the moment that sealed her fate! But little did Marilyn Monroe know that when she sang 'Happy Birthday' to President John F. Kennedy in 1962, it would be the dress that would go on to forever live in the public memory.


The rhinestone-encrusted, flesh-coloured dress is one of the most expensive pieces of personal clothing to ever sell at an auction. Part of a Christie's New York auction in 1999, the glamorous number sold for US$1,267,500.


The silk gauze Jean Louis dress comprised 2,500 crystals and 6,000 rhinestones. And it's been reported that the dress was so form fitting that Monroe had to be sewn into it, which delayed her entry onto the Madison Square Garden stage.


Princess Diana's midnight blue ballroom dress

When it comes to royal style, no other member's wardrobe has been more-talked-about than that of Princess Diana. But perhaps the most referenced pop culture (and fashion) moment in history is the beloved royal dancing with John Travolta at the White House in 1985. And no one could forget Diana's midnight blue, off-the-shoulder velvet dress by couturier Victor Edelstein. It was no surprise that when it went on auction in December 2019, it fetched a whopping US$347,000.


Elizabeth Taylor's jewels

In 2011, Christie's hosted a massive auction of Elizabeth Taylor's most precious jewellery. To date, it is considered the most valuable jewellery auction in history as it generated a staggering US$115,932,000! Among the items up for grabs was a ruby and diamond latticework bib by Cartier – a gift from Mike Todd, Taylor's third husband.

Also featured in the collection was a massive 33.19-carat diamond ring – a gift from Richard Burton (her fifth husband), which she wore daily for more than 30 years. It set a record price per carat selling for US$8,818,500.


Audrey Hepburn's little black dress

Coco Chanel's little black dress remains one of the most influential pieces of clothing in the 20th century. But French designer Hubert de Givenchy's modern interpretation of the concept also garnered massive praise from the fashion community when Audrey Hepburn donned the number in Breakfast at Tiffany's.


The iconic cocktail-style Italian sheath dress ushered the LBD into the 21st century and became one of the most famous dresses of all time, which is why it fetched US$923,187 in a 2006 auction. To date, the piece remains a classic number, thanks to its timeless silhouette and hue that will certainly never go out of style.


Dorothy’s ruby slippers

Every little girl who watched The Wizard of Oz probably dreamed of one day owning her very own pair of ruby slippers like Dorothy's. Reports state that Judy Garland wore about seven pairs of these during filming. One of these remains on display at the Smithsonian in Washington, D.C., while three others have sold at auctions over the years, selling from US$15,000 to US$666,000.


Michael Jackson’s Swarovski glove

Michael Jackson owned multiple versions of his trademark Swarovski-encrusted gloves over the years and many of them have surfaced on the market. But the two most-talked-about ones include the piece purchased by Lady Gaga for US$190,000 in 2012, while another sold for US$350,000 at an auction in Japan in 2009. Furthermore, Jackson's iconic red jacket worn in the Thriller music video also sold for a whopping US$1.8 million.


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