While the celebrity auction market may seem like a recent phenomenon, its roots can be traced back to Americans’ inherent desire to own the things that make other people happy. During the 1950s and 1960s, this desire was fueled by the trend of “pin-up” calendars. These calendars, which feature photos of famous women such as Marilyn Monroe, Betty Grable, Jayne Mansfield and Bettie Page, helped pay for the fashion that the women wore in the photos.

The celebrity auction market is booming, with stars like Janet Jackson, Caitlyn Jenner, and Kim Kardashian all in the buying game. But why? Recent research suggests there are plenty of benefits to charity auctions. For one, the bid money can go a long way toward good causes, and the star’s celebrity status can bring in a lot of attention for the charity and its cause, too, which can continue to raise funds long after the auction is over. Celebrities have also been purchasing charity auctions for a long time, but only recently became very vocal about it, saying that the auctions were a good way to help people.

IN 2015, Julien’s Auctions in Beverly Hills, Calif., sold the fuzzy green mohair-blend sweater that Kurt Cobain wore on Nirvana’s “MTV Unplugged” episode for $140,800. Four years later, the stained cardigan was back on the auction block again. That time it went for $334,000. Today, Darren Julien, the owner of Julien’s, an 18-year-old auction house that frequently hosts sales of celebrity possessions, believes the same grungy sweater could perhaps fetch double that amount. “I’ve had offers of $500,000 to $700,000 to get the buyer to sell it,” he said. For now, the anonymous owner is keeping Cobain’s cardigan. But no matter for Mr. Julien: He has plenty of highly covetable celebrity clothes filling up his auction calendar.

Other auction houses including Heritage and Sotheby’s dabble in pop culture items, but Julien’s is the rare firm which trades almost entirely in nostalgic, celebrity-owned relics. It “specializes in things people don’t need, but things that they want,” said Mr. Julien, including tour-used guitars, furniture from star’s homes and lots and lots of famous clothes. He founded his business four years after financier Martin Zweig paid $1.26 million in a landmark 1999 Christie’s sale to acquire the slinky dress Marilyn Monroe wore to sing “Happy Birthday” to John F. Kennedy. In 2016, Julien’s sold that same beaded, flesh-colored gown on behalf of Mr. Zweig’s widow for $4.8 million.

Earlier this month, Julien’s put on a three-day auction of Janet Jackson’s belongings. The singer is pictured here live-streaming into the auction room.

For Julien’s, the business of auctioning off pop-culturally significant clothes—steady through the mid-2010s—has erupted in the past few years thanks to deep-pocketed 20- to 40-somethings. “Rich millennials don’t want Picasso and Monet. They want pop culture,” said Mr. Julien. “That’s what connects them or, you know, is most appealing to them.”

In January, a set of seven outfits worn by the K-pop band BTS in its 2020 “Dynamite” video sold for $162,500, far exceeding the lot’s $40,000 high estimate. The set was purchased collectively by a pair of Japanese bidders: Yusaku Maezawa, 45, a billionaire and art collector and Hikakin, a 32-year-old YouTuber. A video of the duo joyously winning the auction posted to Mr. Maezawa’s account has been viewed more than three million times.

In April, a pair of Jordan sneakers worn by Bill Murray in “Space Jam” brought in $22,400 during a Julien’s auction.

In April, a pair of Air Jordan sneakers that Bill Murray wore in the 1996 film “Space Jam,” a millennial favorite, brought in $22,400 on a $7,000 high estimate. And just two weekends ago, coinciding with Janet Jackson’s birthday, Julien’s hosted a three-day auction of her belongings, including some of the singer’s seminal early-MTV-era outfits. Julien’s does not disclose buyers’ identities without permission, but a few bidders boasted about their purchases on social media.

Film director and Janet superfan Matthew A. Cherry, 39, bragged on Twitter about snagging Ms. Jackson’s varsity jacket from the 66th Academy Awards. That black coat garnered $2,240, over 11 times its $200 high estimate. And 40-year-old Kim Kardashian boasted on Instagram that she was the buyer of Ms. Jackson’s outfit from her 1993 “If” music video. Ms. Kardashian, who paid $25,000 for the ensemble, gushed online that she was “such a fan” of Ms. Jackson.

Kim Kardashian purchased this ensemble worn by Janet Jackson in the music video for “If” for $25,600.

When Julien’s puts on an auction with a celebrity, as it has done with Ms. Jackson as well as stars like Ringo Starr and Nancy Sinatra, each item comes from the celebrity’s private possession, as opposed to a collector’s stash. Aside from helping stars clear out cast-off costumes and old instruments from their storage space, many celebrities, Mr. Julien said, use the auctions to raise funds for a chosen charity. He said past celebrities have donated anywhere from 10 to 100% of the auction’s proceeds. Ms. Jackson donated an undisclosed portion of the money raised from her auction to Compassion International, a global child-advocacy organization.

Notably, those three aforementioned stars are still alive. Historically, when it came to pop-culture relics, the assumption was that a star’s possessions were more valuable if he or she were dead, but things have changed. Leila Dunbar, who has run an independent appraisal service since 2008, believes that “living-celebrity memorabilia’’ can sell for as much as memorabilia from dead stars, she said. Ms. Dunbar has appraised items for private collectors and museums alike and is one of the few auction-world appraisers specializing in pop-cultural memorabilia—still a relatively niche field compared to the auction market for art.

Ms. Dunbar said that the only thing buyers really care about is having “an emotional connection” to whatever they’re bidding on, be it a Michael Jackson glove or a pair of Pokémon cards.

That emotional pull was what drew David Davis, 69, a retired former art gallerist, to start buying celeb-worn clothing at Julien’s auctions. Mr. Davis purchased his first article from Julien’s in 2009—a hat Barbra Streisand wore in one of his favorite movies, 1972’s “What’s Up Doc?”—and he’s since gone on to buy dozens more. His collection includes the slate gray suit that

Paul McCartney

wore for the photo on the back cover of an early Beatles’ album, Amy Winehouse’s orange-trimmed kimono from the “Rehab’’ video and four outfits of Cher’s. Every piece of clothing spoke to him in some way and triggered a remembrance of the past. For a time he had 20 mannequins around his house all dressed like his favorite stars. “I had to give tours,” when guests came over, he said.

David Davis, a frequent Julien’s bidder, displayed his celebrity clothes, such as this ensemble worn by Barbra Streisand, around his house on mannequins.

Not all buyers are driven by sentiment though. Mr. Julien is aware of hedge fund managers who are carving out money in their portfolios to invest in pop culture, and he’s heard from buyers who are now treating celeb-memorabilia as a pure investment.

In recent years, Mr. Davis has spent less on celebrity clothes. The market simply got too frenetic. Mr. Davis personally is now more interested in collecting historic photographs, a market that so far has been less competitive.

As for Julien’s, its business has only exploded further during the pandemic. During Covid, Julien’s has live-streamed all of its auctions and Mr. Julien sheepishly noted that this was one of his house’s strongest years yet.

To meet the demand, Mr. Julien has a full slate of auctions ahead including one this June dedicated to musical icons. That auction’s catalog dropped today and includes bid-baiting celebrity clothes like a tan double-breasted suit worn by Mick Jagger in the ‘70s and striped glasses worn on stage by Elton John.

Write to Jacob Gallagher at [email protected]

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