10 of the Most Expensive Clothes Ever Sold

We have rounded up ten of the most expensive clothes ever sold.   

1. Marilyn Monroe's "Happy Birthday, Mr. President" Dress: $4.8 Million 

On May 19, 1962, America’s beloved blonde bombshell, Marilyn Monroe, took the stage at Madison Square Gardens to give President John F. Kennedy a birthday serenade. The dress she wore—a custom-made Jean Louis gown—would later be purchased for $4.8 million in 2016. Today, the garment holds the Guinness World Record for the most expensive dress sold at auction.  

2. Dorothy’s Ruby Slippers: $666,000

In the 1939 blockbuster “The Wizard of Oz,” Dorothy’s ruby slippers possess powers that ward off the Wicked Witch and transport her back to Kansas. Alas, the real shoes—crafted from red silk faille overlaid with red-sequined georgette—don’t offer the same magical powers. Nevertheless, they still sold for $666,000 in 2000. 

3. Indian Prime Minister Narendra Damodardas Modi’s Suit: $693,174

This monogrammed, pinstriped suit was worn by Indian Prime Minister Narendra Damodardas Modi during President Barack Obama’s second state visit to India. Though initially criticized for being over-the-top, the garment scored a pretty penny at auction in 2015. The proceeds benefited the Namami Gange Fund, a project to clean the Ganges.  

4. Audrey Hepburn’s “Breakfast at Tiffany’s” Dress: $807,000

An icon of female femininity, the Givenchy sheath worn by Audrey Hepburn in the film "Breakfast at Tiffany's” forever changed the history of the little black dress. Suddenly, women ‘round the world traded in their full skirts and rounded shoulders for a simpler and sexier silhouette. Long story short, this dress is greatly revered in the fashion world. Hence its $807,000 price tag at a London auction in 2006. 

5. Michael Jackson's “Thriller” Jacket: $1.8 Million

Michael Jackson's thriller jacket 

In 1982, Michael Jackson shook the music world with his soul-meets-rock-meets-pop album, “Thriller.” It has since sold 70 million copies worldwide, taking the Guinness World Record for the best-selling album. And so, it only makes sense that the artist’s “Thriller” jacket—a black and red calf leather garment with winged shoulders—took home a Guinness World Record for the most expensive jacket sold at auction after fetching $1.8 million in 2011.   

6. Michael Jackson’s Moonwalk Glove: $420,000

M.J. makes the list once again for the sparkly, rhinestone-studded glove he wore when he debuted his first moonwalk dance in 1983. The performance, which was aired on the “Motown 25: Yesterday, Today, Forever” television special, obviously made an impression. In 2009, just a few months after the pop star's death, a Hong Kong businessman purchased the mitt for $420,000.     

7. “I Love Lucy” Dress: $168,000

Avid collector James Comisar loves “I Love Lucy.” Like a lot. Because during a Hollywood memorabilia auction in 2013, Comisar purchased the tailored, black-and-white, polka-dotted dress Lucille Ball wore as Lucy Ricardo for an eye-boggling $168,000. The final purchase price was $100,000 more than auctioneers expected.      

8. 1972 Nike Moon Shoe: $437,500 

What do waffles and sneakers have in common? The 1972 Nike Moon Shoe, apparently. Some 50 years ago, Nike co-founder Bill Bowerman was tinkering with his wife’s waffle iron when a lightbulb went off. He ran out, grabbed some rubber, and poured it into the kitchen appliance to create a prototype of the shoe’s sole. A dozen pairs of the sneakers were created for the 1972 Summer Olympics, one of which sold for a whopping $437,500 in 2019. 

9. Levi Strauss & Co. "XX" Blue Denim Trousers: $100,000

Compared to a $4.8 million dress, these blue denim trousers by Levi Strauss & Co. are a steal. Plus, they have a darn good story. Manufactured in 1893, these pants were purchased by a larger-than-life character named Solomon Warner. An American entrepreneur with a thirst for gold, Warner settled in Arizona in 1856. He lived there the rest of his life, ordering this particular pair of trousers when he was 80 years old. In 2018, they were purchased by an anonymous collector for six figures. 

10. 1967 Grateful Dead Tee: $17,640

Deadheads are a loyal troupe. Case in point: Enthusiast Bo Bushnell paid $17,640 (before taxes and fees) for this garment in 2021. Designed by Hells Angel and graphic artist Allan “Gut” Terk, the mustard-yellow tee set a new record as the most expensive vintage rock shirt sold at auction.     

At Myles Price, we believe clothing should be understatedly elegant—quiet in its subtle sophistication. Such is the heart of our LuxCasual brand. But alas, we still like to ogle at over-the-top garments that fetch a pretty penny.