Inside Cyndi Lauper’s Fashion Archive: The Stories Behind Her Most Unforgettable Looks

Before she was a pop star, she was ringing up customers at a downtown vintage shop. Now, decades of her daring looks are up for grabs, and each one comes with a story.

Cyndi Lauper’s style was never conservative. The singer had a penchant for bold, colorful looks, and fans now get a chance to own a piece of her fashion in an auction dubbed “Cyndi Lauper: Suitcase of Memories.”

The two-part auction featuring her personal items and memorabilia includes a live sale in New York on October 22 along with an online sale running through October 23. The event is a collaboration between Lauper and the auction house Bonhams.

“I did this to inspire people,” Lauper told The Guardian of the exhibit. “To inspire us who are older to remember the individuality of creativity, and to inspire the young to discover that creativity is individual.”

Lauper’s love of fashion runs in the family. She grew up in Queens with a large family working as cutters and seamstresses in New York’s Garment District. She developed her eclectic style when she worked as a cashier at Screaming Mimi’s, an edgy vintage boutique in Manhattan. While doing this, she was also singing in local clubs.

Lauper would eventually delight fans with her music, capturing a generation who saw her complementing her music with her own sense of fashion.

Some of her most famous outfits included the leopard print pajamas she wore in the “Girls Just Want to Have Fun” video, which were her grandmother’s and came from Frederick’s of Hollywood, a family-favorite mail-order catalog.

And who can forget the newspaper skirt she wore for “True Colors”? Finding it again for the auction made her emotional. “When I found the paper skirt, I cried,” she told People. “We brought it back to life, me and Laura Wills, who helped me curate the collection.” Chappell Roan even wore a replica of the skirt when she inducted Lauper into the Rock and Roll Hall of Fame

Lauper also had a gift for adding her own twist to designer fashion. In the 1990s, she would wear pieces from Vivienne Westwood and Alexander McQueen and add her personal touches to them. For her 1994 album “Twelve Deadly Cyns,” she paired an electric blue Dolce & Gabbana shrug with a bowler hat she spray-painted and decorated with feathers to match. “I wanted it to look like art,” she said.

Other pieces in the collection include the metal bra and headdress from her “True Colors” video, a red plaid dress she wore to the first MTV VMAs, and even furniture from her New York City apartment.

Now in her 70s, Lauper remains true to her bohemian style. “I’m 73. But I don’t want to look conservative, and you don’t have to,” she told People. “I think I always love to embrace bohemia because that’s where the artist live. That’s where the creatives came from.”

Most of all, she hopes her archive inspires the younger generation. “That’s what makes it exciting,” she told The Guardian. “That a young person would look and go, ‘I could do that.’”