The 16 Priciest Fashion Items Ever Sold at Auction

One of the more memorable dresses Princess Diana wore, a sequined Catherine Walker evening gown, is currently up for auction and experts believe it will fetch around $145,000. The late Princess wore this dress on more than one occasion — during a state visit to Austria, to the Diamond Ball, and to the 1993 Biggles film premiere.

Worn by Princess Diana to the film premiere of James Bond's The Living Daylights, this Emanuel Bakst-inspired ball gown sold at auction for £102,000 in 2013. Decorated with gold sequins, crystals and pearl beads, it comes with matching headband, optional sleeve panels and petticoat.

Who could forget the off-the-shoulder midnight blue Victor Edelstein velvet dress Princess Diana wore to the White House in 1985? A shining example of her classic elegance, the dress sold at auction for $360,000 in 2013.

A little less glamorous than Diana's dresses but perhaps more historic are a number of pairs of bloomers that once belonged to Britain's Queen Victoria. Dating back to the 1890s, this particular pair of royal knickers was sold at action in 2009 for $7,200. Another pair with a much smaller waistband sold at auction in 2011 for $15,000.

Dorothy's blue and white pinafore and blouse is one of the most iconic pieces of clothing in film. Worn by Judy Garland in the classic The Wizard of Oz, the dress sold for $480,000 in 2012 at an auction by Julien's Auctions in Beverly Hills.

What little kid didn't dream of one day owning her own pair of ruby slippers, like The Wizard of Oz's Dorothy? It's speculated that between six and seven pairs of these storied slippers were created for Judy Garland to wear during filming, and while the pair she primarily wore for her dance numbers is on display at the Smithsonian, three other sets have appeared at auction over the years selling for between $15,000 to $666,000.

Many Halloween costumes have been inspired by the pleated white dress created by costume designer William Travilla for Marilyn Monroe in The Seven Year Itch. Considered one of the most iconic Hollywood images of the 20th century, the dress sold for $5.6 million at the Debbie Reynolds auction in 2011.

Arguably the song that sealed her fate, the unbelievably sexy rhinestone-encrusted, flesh-coloured dress that Marilyn Monroe wore when she sang "Happy Birthday, Mr. President" is one of the most expensive pieces of personal clothing to ever sell at auction. Part of a Christie's New York auction in 1999, the skin-tight number Monroe was said to have been sewn into sold for $1,267,500.

In 2011, Christie's hosted a massive auction of Elizabeth Taylor's most precious jewellery — now considered the most valuable jewelry auction in history generating $115,932,000! Of the items up for grabs were this ruby and diamond latticework bib by Cartier which was a gift from Mike Todd, Taylor's third husband, in 1957.

This massive 33.19 carat diamond set a record price per carat selling for $8,818,500! The ring was a gift from Richard Burton, her fifth and sixth husband, which she wore daily for more than 30 years and rightfully earned its nickname.

Designed by Givenchy, a close friend of Audrey Hepburn at the time, the iconic black dress in Breakfast at Tiffany's sold for $923,187 in 2006. The Italian satin sheath gown is marked by it's distinctive cut-out back, gathered waist and slit to the thigh.

Another Hepburn classic, the intricate Cecil Beaton dress worn by the actress in My Fair Lady sold at auction for an impressive $3.7 million.

Who could forget that silly hat Pharrell wore to the 86th annual Academy Awards? First spotted on the red carpet at the Grammys, the Vivienne Westwood "mountain hat" retails for $180 on Westwood's online shop. That didn't stop bidders from forking over a shocking $44,100 to get their hands on the actual hat that host Ellen DeGeneres passed around during the show collecting tips from the likes of Brad Pitt and Harvey Weinstein. Proceeds from the sale went towards the non-profit From One Hand to AnOTHER. 

The infamous gold bikini worn by actress Carrie Fisher in Return of the Jedi sold for a whopping $96,000 at auction. The lucky bidder who purchased the slave costume also received a collar and several chain links.

Like the ruby slippers, Michael Jackson's trademark glove was made in multiples meaning a number of them have surfaced on the market over the years. In 2012, Lady Gaga claimed to have picked up a Swarovski-encrusted one for $190,000 while another sold for $350,000 at an auction in Japan in 2009.

Another popular Halloween costume, the iconic jacket worn by Michael Jackson in the "Thriller" video surely set a trend for red leather jackets. In 2011, the original was auctioned off by Julien's Auctions, selling for a whopping $1.8 million.