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There are bags, and then there’s the Birkin. No other accessory carries the same weight, emotion, and mythology. Designed by an icon, for an icon, and named in her honour, the Birkin has become a symbol of status, legacy, and obsession.
The recent sale of the very first Birkin ever made for an astonishing $10 million made headlines around the world. But it’s far from the only fashion artefact to fetch a jaw-dropping price. Over the years, collectors have fought over everything from sunglasses to cardigans, not for utility, but for the history they carry.
So what makes a piece worth millions? Is it being the first of its kind? Is it about rare materials? Or does its value come from its connection to a cultural icon? More often than not, it’s a blend of all three: origin, meaning, and myth.
Here are just a few of the most legendary fashion items and accessories to ever hit the auction block:
Paul Newman’s Rolex Daytona – $17.8 Million (2017)
The holy grail of vintage watches. Gifted by Joanne Woodward and worn daily by Newman, this 1968 Daytona redefined what a watch could mean. The ultimate combination of craftsmanship and character.
Princess Diana’s black Sheep Sweater – $1.1 Million (2023)
Whimsical, defiant, and deeply personal, this red Warm & Wonderful sweater featuring a single black sheep became one of Diana’s most iconic looks. Worn in 1981 and rediscovered decades later, it broke records for the most expensive sweater ever sold.
Nike “Moon Shoe” Prototype – $437,500 (2019)
One of the first sneakers ever made by Nike co-founder Bill Bowerman using a waffle iron. Only 12 exist. The Moon Shoe marked the beginning of sneaker culture as we know it.
Elizabeth Taylor’s La Peregrina Pearl Necklace – $11.8 Million (2011)
A pearl fit for a queen… and worn by one. Originally discovered in the 16th century and once owned by Spanish royalty, this historic gem was gifted to Taylor by Richard Burton. She had it redesigned by Cartier with rubies and diamonds, and when it went to auction, it became the most expensive pearl necklace ever sold.
Michael Jackson’s “Bad” Tour Jacket – $288,000 (2018)
This black and gold military jacket was (and still is) a time capsule of 1980s pop culture and theatricality.
Steve McQueen’s Tag Heuer Monaco – $2.2 Million (2020)
Worn in Le Mans and forever linked to McQueen’s rugged cool, this watch carried attitude that only someone like McQueen could match.
Kurt Cobain’s MTV Unplugged Cardigan – $334,000 (2019)
Worn during one of the most intimate performances of the 1990s, the cardigan, burn holes and all became a sacred relic of grunge.
John Lennon’s Round Glasses – $183,000 (2019)
Sold by his former chauffeur, these gold-rimmed frames are now shorthand for Lennon’s vision, intellect, and legacy. A quiet piece with loud meaning.
Freddie Mercury’s Crown and Cape Set – $810,000 (2023)
Fit for rock royalty, this rhinestone-studded set from Queen’s final tour turned a stadium into a throne room.
Elton John’s Wardrobe and Accessories – $8 Million (2024)
From custom Versace suits to glitter-drenched sunglasses, Elton’s personal Christie’s sale included over 900 items of pure flamboyant glam. His star-shaped Cartier cufflinks and Gucci bags are true pieces of pop history.
It might still be baffling to some that items like these sell for millions of dollars, but they are snapshots of a bygone time and culture, one that continues to be admired. They were lived in, performed in, and remembered. And in the world of fashion, that kind of meaning is priceless.
