Each June, Royal Ascot transforms into a global fashion show of headwear, where tradition and spectacle meet strict dress codes and creative expression. In 2025, the event continues its legacy as a proving ground for milliners and fashion houses, with hats serving as both status symbols and artistic statements.
The fascination with extravagant headpieces is rooted in centuries of history, from aristocratic rituals to modern luxury auctions. Over time, certain hats have gained legendary status due to their association with notable figures, exceptional craftsmanship or unique materials. These hats often command extraordinary prices at auctions and private sales, reflecting both their rarity and cultural significance.
Here, WWD takes a closer look at the history behind the most expensive hats in history.
Princess Beatrice’s 2011 Royal Wedding Hat: $130,710
Princess Beatrice attends the wedding of Prince William and Kate Middleton at Westminster Abbey on April 29, 2011, in London.
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Princess Beatrice‘s now-infamous fascinator, designed by Philip Treacy, was worn by the British royal family member to the wedding of Prince William and Kate Middleton in April 2011. The hat was the fixation of fashion scrutiny. Instead of hiding the hat away, Princess Beatrice turned the hat’s meme-ability into an opportunity to raise money for charity. The royal auctioned off the hat on eBay, according to NPR, selling it for $130,710 at auction.
Andy Warhol’s “Money Hat”: $1.2 Million
Andy Warhol (1928-87) at the Ritz Hotel in London to promote the film “Trash,” directed by Paul Morrissey and produced by himself on Feb. 15, 1971.
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Andy Warhol created the “Money Hat” in 1972 for his friend, Dr. Robert Giller, for his 30th birthday, according to ArtNet. The construction featured a black straw Halston hat with a band of $10 bills creating the exaggerated brim. Warhol signed one of the $10 bills himself. In November 2015, the hat resurfaced. With an estimated value between $800,000 and $1.2 million, the hat was sold at auction by NYE & Company.
Napoleon Bonaparte’s Bicorne: $2.1 Million
The bicorne black beaver hat on auction belonged to Napoleon Bonaparte.
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One of Napoleon Bonaparte’s iconic black-felt bicorne hats was sold at auction in 2023 for $2.1 million. The collection of bicorne hats, dating back to the 1800s, featured multiple owners. The bicorne hat sold in 2023 was previously owned by Colonel Pierre Baillon, a military officer, antiques dealer Charles Meyer and Jean Brunon. The latter received the 1928 auctioned bicorne and passed it down through his family, according to CBS News.
Chapeau D’Amour: $2.7 Million
Alicia Witt models the most expensive hat ever made, on June 14, 2004, in London.
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The famous Chapeau D’Amour was created by milliner Louis Mariette in 2004. The “Hate of Love” was crafted from woven platinum fabric and embellished with diamonds and amethysts. With sinuous curves and an extravagant shape, the hat features a sculptural quality evocative of feathers. The hat has never been sold but is estimated to be worth $2.7 million.
The Papal Tiara: Priceless
Members of the media look at Papal Tiaras from the Sistine Chapel at the fashion exhibit “Heavenly Bodies: Fashion and the Catholic Imagination” at The Metropolitan Museum of Art on May 7, 2018, in New York.
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Papal tiaras from the Sistine Chapel were featured as part of The Metropolitan Museum of Art’s 2018 fashion exhibit “Heavenly Bodies: Fashion and the Catholic Imagination.” These historic pieces are crafted with diamonds, rubies, sapphires and more gems. Housed in Vatican City, the tiaras have never been auctioned, but are estimated to hold a value well within the millions.