Legendary Fashion Collectibles That Defined Auction History

It’s not uncommon for rarefied paintings and exceptional sculptures to fetch millions at auctions—however, even fashion collectibles and memorabilia have reaped astronomical sums at the world’s most prestigious auctions—from limited edition luxury handbags to haute couture. Over the decades, couture dresses worn by pop-culture icons such as Marilyn Monroe and Princess Diana have managed to dazzle the auction block, commanding strapping sums at both public and private sales. Not long ago, veteran French actress Catherine Deneuve auctioned off her Yves Saint Laurent couture collection at Christie’s for more than $ 1million. While we’re on the topic, the Birkin frenzy in the auction space merits a special mention. Renowned for their savoir-faire, Himalaya Birkins are a rare find for serious collectors and are always in demand with or without diamonds. Himalaya Birkins generally sell at higher prices in the secondary market than other crocodile Birkin bags depending on the condition and age of the bag. In 2021, the Himalaya Birkin 25 was of the most desirable size and sold for over $300,000 at Sotheby’s. Here’s looking at some of the noteworthy fashion collectibles which eclipsed at all other auctions.

Birkin 20 Matte Alligator

Unveiled in 2023, this appeared at an auction held in Sotheby’s October 2023 Hong Kong sale. The Birkin 20 in Vert D’eau Matte Alligator in a more structured Sellier with Gold Hardware sold for HKD 889,000 or $115,570. While the bag silhouette and Sellier structure are a lot like the Faubourg, the body of the bag is unadorned. A black lizard Birkin 20 sold for HKD 600,000 or $78,000 in October 2024.

Marilyn Monroe’s Dress And Watch

The dress and wristwatch worn by Marilyn Monroe during her famous performance of ‘Happy Birthday Mr. President’ for then-President John F. Kennedy in 1962 were sold at an auction for a combined $5m. Monroe’s Madison Square Garden performance became iconic in mainstream culture in the decades since it occurred, thanks in part to incessant rumours about her alleged involvement with Kennedy. The performance took on an added significance when Monroe died of a drug overdose less than three months later, aged only 36.

A Rare Paco Rabanne ‘Armour’ Dress, 1967

One of the most iconic and instantly identifiable designs by Paco Rabanne exuded a futuristic vibe and embodied metal construction. Reminiscent of the mod 1960s minimal approach to design at a time when the world was fascinated by space exploration having put a man on the moon, this was sold for £37,000 at Kerry Taylor auctions in 2020

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Patek Philippe 5208T

Crafted especially for Monaco’s famed Only Watch auction—the biennial charity auction of luxury timepieces that raises funds for research into Duchenne Muscular Dystrophy—the Patek Philippe Titanium 5208T sold for $6.23m in November 2017. A one-of-a-kind titanium version of the 5208 model, it was crafted using an inky blue colour palette and features a sapphire-crystal case-back, hand-guilloché details, gold indexes and an 18K gold dial plate.

Muhammad Ali and Sonny Liston’s Boxing Gloves

Muhammad Ali (named Cassius Clay at the time) and Sonny Liston’s 1965 meet-up made boxing history for its “phantom punch”. The gloves worn by both athletes in the controversial fight also went down in history as some of the most expensive, costing one sports fan $956,000 in a 2015 auction.

Steve McQueen’s ‘Le Mans’ Suit

Sold for $336,000 at the 2017 Sotheby’s auction was the Gulf racing suit worn by McQueen’s character Michael Delaney. Stored for much of the past 46 years, this suit is still unbelievably original with light staining from storage. The helmet has been repainted in the period as it was used as a daily motorcycle helmet for a few years. Both the helmet and jacket have lead seals attached, believed to have been added by Solar Productions’ Costume department, whilst the helmet features all of the correct and original labels from Bell and the Snell Foundation.

Audrey Hepburn’s ‘Breakfast at Tiffany’s’ Dress

Estimated to go for as little as £50,000, the iconic Givenchy look went beyond expectations at a 2006 Christie’s auction. The sleeveless black satin gown worn by Audrey Hepburn as Holly Golightly (and later Natalie Portman on the cover of Harper’s Bazaar) officially sold for £467,200, or around $920,000.

Chanel Coat

Part of Mouna Ayoub’s (French socialite and businesswoman) vast haute couture collection, the “Coromandel” design by Karl Lagerfeld for Chanel was the star lot at Maurice Auction’s sale. Mouna Ayoub’s auction of the seminal piece from her vast collection of Chanel haute couture was a hit. Maurice Auction sold all 252 lots at the Pavillon Gabriel in Paris, netting 1.5 million Euros, with one evening coat—embroidered by Lesage to resemble the ornate Coromandel screens that founder Gabrielle Chanel so treasured—fetching 312,000 Euros, according to a spokeswoman for the sale. Part of the star lot, the coat was estimated to fetch between 150,000 and 200,000 Euros.

Princess Diana’s Victor Edelstein Gown

In 2019, the black velvet Victor Edelstein gown worn by Princess Diana was sold for $290,000. It was purchased by The Historical Royal Palaces. The late royal wore the outfit while dancing with John Travolta at the White House in 1985.

Hermès Feather Mosaïque Kelly

This taupe Sellier Kelly, made in 2010, comes adorned with a geometric collage of multi-hued plumage. It sold for $352,825 at a 2021 Christie’s auction in Hong Kong.

Elizabeth Taylor’s Gold And Diamond Evening Bag

In 2011, Christie’s sold several items that once belonged to actress Elizabeth Taylor. The auction’s priciest item was this woven gold clutch embellished with diamond lettering. It was sold for $218,500.

A Rare Elsa Schiaparelli couture gold lamé waistcoat, 1936

Sold for £800 in 2022 at an auction in the US, the same waistcoat is photographed in Harper’s Bazaar, September 1936 issue, captioned: ‘…and a new race of sleeved evening dresses worn with little fitted jackets’.

Chanel Diamond Forever Bag

In 2008, Chanel produced its Diamond Forever bag. Karl Lagerfeld designed the alligator leather piece in the style of the French label’s iconic flap bags. It features white gold hardware, including a clasp encrusted with 334 diamonds totalling 3.56 carats. The Diamond Forever was put up for auction during amfAR’s Cinema Against AIDS benefit, selling for $261,000.

Audrey Hepburn’s ‘My Fair Lady’ Dress

Part of Debbie Reynolds’ estate, Audrey Hepburn’s glorious “Ascot dress” went up on the auction block in 2017 and sold for $4,551,000. Costume designer Sir Cecil Beaton had won an Academy Award for his work on the 1964 film.

Michael Jordan Sneaker Collection

In February 2024, a collection of sneakers that superstar Michael Jordan wore as he and the Chicago Bulls won six NBA championships fetched $8 million at the auction, setting a new record for game-worn sneakers, Sotheby’s said. The six Air Jordan shoes — one apiece from the last games of the 1991, 1992, 1993, 1996, 1997 and 1998 championship series—sold at Sotheby’s, were dubbed as the “Dynasty Collection.”

Paul Newman’s ‘Exotic’ Rolex Daytona

The Hollywood icon’s ‘Exotic’ Rolex Daytona was sold in New York in 2017 for a record-breaking $17.75m. Newman was partial to the Rolex’s iconic Daytona model (built for timing car races), a number of his timepieces have broken records but this one from 1968 was particularly extraordinary. Given to Newman by his wife, it is engraved on the back with the words ‘Drive Carefully Me’ following his 1965 accident. The actor was subsequently pictured wearing the watch regularly, including at high-profile races.

A Rare Hooded Dress By ALAÏA

Dating back to 1986, it was crafted out of sage-green knitted wool, with the zip following the contours of the body in a spiral from neck to hem. Christie’s estimate was between £800 – £1,200 and the price realised was £9,375.

Catherine Deneuve’s Yves Saint Laurent Couture Collection

The French silver screen legend auctioned her Yves Saint Laurent couture collection at Christie’s for more than $1 million (£785,887). She was a muse to the designer as well as a close friend for 40 years (she recited a poem at his funeral in 2008) and many of the pieces in the collection date back to the 1960s and 1970s when Laurent dazzled the fashion industry with the invention of Le Smoking.