The Most Expensive Clothing Items Ever Auctioned

In most cases, used clothing is found in consignment shops and secondhand stores at bargain prices. But depending on who wore it, the most highly coveted fashion items can score five-, six-, and even seven-figure bids at auction houses like Christie's, Sotheby's, and others. Among them is the deep purple gown Princess Diana wore in her Vanity Fair spread that fetched more than five times the auction estimate.

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Queen Victoria was Great Britain's second-longest serving monarch and in 2015, a very intimate article of the queen's clothing fetched the equivalent of nearly $14,000 at auction. Her majesty's so-called big pants, complete with a personalized, embroidered monogram, were dated to the 1890s. Experts came up with that estimate by examining the photographic record, which led them to conclude that era is when the queen had acquired the 45-inch waistline that her bloomers were designed to accommodate.

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In 2018, a single sneaker in terrible condition sold at auction for more than $90,000 — but it was hardly just any sneaker. It was one of the original Nike Air Mags worn in “Back to the Future II” from 1989. The dilapidated sneaker attracted 220 bids on eBay and fetched just shy of six figures despite a crumbling heel, a cracked midsole, and a detached outsole.

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Carrie Fisher's Princess Leia serving as Jabba the Hutt's chained, bikini-clad slave has stoked nerd fantasies for more than 35 years since the premiere of Episode VI of the Star Wars franchise. In 2015, a year before Fisher's death, an anonymous bidder shelled out $96,000 for the costume, which came complete with Leia's collar and chains.

The arrival of Kate Middleton ushered in a new era of refined elegance in British Royal history. In 2002, the Duchess of Cambridge wowed audiences at a London fashion show with a see-through knitted mesh slip that left little to the imagination. In 2011, an anonymous British man coughed up more than $100,000 to add the item to his collection.

In 2012, a charity auction raised $5 million after bidders dug deep to get their hands on some of the most iconic pieces of clothing Michael Jackson ever wore. Among the biggest draws were the King of Pop's gloves, signed loafers, and tour shirts. The one item that fetched the most out of the entire lot, however, was a jacket he wore during the 1987-1989 Bad tour when Michael Jackson was arguably the most famous person on Earth. In 2018, a signed Bad tour jacket sold at the Icons & Idols: Rock-N-Roll auction in New York, this time for $289,000.

When Princess Diana visited Ronald Reagan in the White House in 1985, the People's Princess shared a famous dance with legendary rug-cutter John Travolta. The velvet gown she wore that evening sold for $360,000 at a 2013 auction, the biggest winner of a selection of the Princess' dresses that fetched a total of $1.2 million.

The “Moon Shoe” is one of the most important pieces of Nike history, and its genesis is the stuff of Nike legend. Oregon University track-and-field coaching icon Bill Bowerman co-founded Nike and experimented with the now-famous running shoe’s sole traction by pouring rubber into his wife’s waffle iron. Called the Moon Shoe because its print resembled those left by the Apollo 11 astronauts on the moon, the originals were hand-cobbled by Geoff Hollister, an original Nike employee. Only about a dozen were ever made, about half of which are still around today. The pair that broke the auction record is the only unworn pair on Earth.

The deep purple silk velvet dress that Princess Diana donned for her official portrait in 1991, and more famously in a Vanity Fair spread just before her death in 1997, sold at a Sotheby's auction for $604,800, more than five times the $120,000 auction estimate. The strapless Victor Edelstein gown features a sculpted sweetheart neckline and a tulip skirt and was last sold in 1997 for $24,150 at a charity auction of dresses donated by Diana. Vanity Fair at the time called it "a powerful symbol of her changing life" during her tumultuous divorce from Prince Charles.

Thanks to the ESPN documentary “The Last Dance,” 2020 saw a huge revival in Michael Jordan fever and an equally high demand for the choicest Jordan memorabilia. In August, just a few dreary months after the first pair of game-worn 1s broke all previous records in May, a different pair snagged the trophy. In this case, it was a pair of 1985 Jordan 1s that No. 23 wore when he famously shattered the backboard during a pre-season game in Italy. The pair was the crown jewel in the 2020 Original Air auction.

Audrey Hepburn played Holly Golightly in the 1961 blockbuster "Breakfast at Tiffany's." When it sold at auction in 2006, the famous black Givenchy dress she wore on the big screen commanded more than $800,000, a price tag that shocked industry experts. The dress sold for nearly six times the highest presale estimates.

Over the course of two days in 2013, a bidding war raged at an auction in Hollywood. Among the most prized pieces were a collection of costumes from the 1965 classic "The Sound of Music." The lot, which included famous garments such as Julie Andrews' brown "Do-Re-Mi" dress and the drapery outfits worn by the Von Trapp children, shocked industry insiders by selling for $360,000 more than the highest presale estimates.

In 2015, $1.6 million was also the final bid on another iconic piece of clothing, this time at an auction in New York. That year, one deep-pocketed collector went home with the blue-and-white gingham apron and shirt made famous by Judy Garland, who wore the combo as Dorothy in "The Wizard of Oz."

In 1982, pop culture, pop music, music videos, and fashion changed forever when Michael Jackson released the "Thriller" album. The single most visible object from that moment in history is the black-and-red leather piece of outerwear known forever as the "Thriller jacket." In 2011, a gold trader from Texas made it his own when he shelled out $1.8 million to add it to his collection.

One of the most expensive items ever to sell at auction was, once again, first worn by Audrey Hepburn. This time it was the Ascot dress she donned in 1964's "My Fair Lady." The item was part of an astonishing collection amassed by screen legend Debbie Reynolds, who spent a half-century collecting tens of thousands of photographs, articles of clothing, props, and other famous keepsakes from some of the biggest movies in history. Her collection, considered the most significant in the world, was liquidated in 2011 through a series of Profiles in History auctions.

In the history of pinup-girl sex symbols, one iconic image stands out above them all: Marilyn Monroe struggling to keep her white dress down while standing over a drafty subway grate. The image comes from the movie "The Seven Year Itch," as does the dress, which sold for more than $4.5 million at a 2011 auction in Beverly Hills.

Marilyn Monroe's "The Seven Year Itch" dress was the most expensive dress ever sold at auction for five years until a different one stole the record at Julien's Auctions in 2016. The dress was different, but the person who wore it was not. The most expensive dress ever sold at auction is the one worn by Marilyn Monroe when she famously sang a sultry version of "Happy Birthday" to President John F. Kennedy in 1962.