Cyndi Lauper Auctions Iconic 1980s Outfits That Made History

Emma Caldwell
October 10, 2026

There are artists we remember for a song and others whose image is almost as recognizable as their music. Cyndi Lauper clearly belongs to the second group. The colored hair, the stockings, the corsets, the overlapped dresses, the jewelry worn without restraint, and that seemingly impossible mix of vintage garments helped build an aesthetic that we still identify today with the 1980s.

That’s why it’s somewhat of a small event that much of that wardrobe is now going to auction. Bonhams presents Cyndi Lauper: Suitcase of Memories, a two-part sale that brings together fashion, accessories, stage costumes and personal objects preserved for more than four decades of her career. The first will take place in New York on October 22 and will consist of 20 lots, while a second auction will be held online until October 23.

The wardrobe with which Cyndi Lauper changed the 80s aesthetics

Cyndi Lauper never understood fashion as something separate from music. She herself has explained it when presenting the auction: reviewing her archive allowed her to remind all the collaborators who participated in building her image and to reunite three worlds that, for her, have always been connected: art, fashion, and music.

“For me, fashion is art,” the singer asserts about the collection. The sale is additionally especially symbolic because it coincides with the 40th anniversary of True Colors, her second album, released in 1986.


Cyndi Lauper turned the blend of vintage garments, accessories and theatrical references into one of the most instantly recognizable images of the 1980s.

And precisely from that era comes one of the auction’s major protagonists: the famous skirt made of strips of newspaper that she wore on the True Colors cover and in the song’s music video.

The piece is one of the clearest examples of the aesthetic that Lauper developed with Laura Wills, founder of the New York vintage shop Screaming Mimi’s and responsible for many of those early looks. Bonhams estimates the ensemble at between 1,000 and 2,000 dollars.

From leopard-print pajamas to the dress she wore at the first MTV Video Music Awards

The newspaper skirt isn’t, however, the only garment with a story behind it. Among the lots is also the leopard-print pajama that Cyndi Lauper wore in the video for Girls Just Want to Have Fun, perhaps one of the songs that best encapsulate the spirit of that decade. Its estimate is between 500 and 700 dollars.

Also up for sale is the red plaid dress and the jewelry she wore at the first edition of the MTV Video Music Awards, held in 1984 at the Radio City Music Hall in New York. That night Lauper accrued nine nominations and ended up taking the Best Female Video award precisely for Girls Just Want to Have Fun. Bonhams estimates the ensemble at between 800 and 1,200 dollars.

Another lot takes us back to True Colors. The singer still preserves the golden metal bra and part of the jewelry she wore in the video, as well as during a photo shoot by Matthew Rolston for Interview in 1986. The image was inspired by a 1923 photograph of silent film actress Mae Murray and ended up becoming one of the most theatrical looks of that era.

In this case, the lot includes the bra, a rhinestone-embellished shoulder pad, necklaces, chains and an ornate belt. Its estimate is between 1,000 and 1,500 dollars.

Vivienne Westwood also part of the auction

The archive also shows that Lauper’s style was not limited to vintage garments. Among the big names appearing in her wardrobe is Vivienne Westwood, a designer with whom she shared that unconventional way of understanding fashion.

Bonhams is auctioning a green fringe ensemble from Westwood’s 1985 Spring-Summer collection that Lauper wore in 1986 during a Late Night with David Letterman appearance, where she performed True Colors. Its estimated price is between 800 and 1,200 dollars.

The collection also spans later stages of her career and includes designs by brands such as Alexander McQueen, along with stage costumes, accessories, awards and various personal objects.


Décadas después de sus primeros grandes éxitos, Cyndi Lauper ha seguido utilizando la moda como parte esencial de su identidad sobre el escenario

An aesthetic that remains recognizable four decades later

Perhaps the most interesting aspect of the auction isn’t only the names or the value the garments may fetch. It is to understand to what extent the clothing helped to build the character of Cyndi Lauper.

Her wardrobe mixed punk, vintage garments, corsets, theatricality, references to old Hollywood and a huge amount of accessories. A formula very different from the idea of refined elegance that dominated other areas of fashion, but one that ended up defining a part of the popular aesthetic of the 80s.

And there is good proof that those images still work. Four decades later, simply mentioning a newspaper-constructed skirt, a leopard-print pajama, or a red plaid dress instantly brings you back to the world of Cyndi Lauper.

Emma Caldwell
Emma Caldwell
I’m Clara Desrosiers, a writer and fashion editor based in Toronto. I founded Backdoor Toronto to explore the intersection of fashion, identity, and culture through honest storytelling. My work is driven by curiosity, community, and a love for the creative pulse that defines this city.