When Madonna and Sean Penn traded vows beneath a white tent perched in Malibu, Calif., on Aug. 16, 1985, their guest list doubled as a living fashion time capsule. The high-profile wedding welcomed Hollywood’s elite in outfits that captured a decade defined by bold choices, wild silhouettes and unapologetic self-expression.

“It was the right mixture of nobodies and celebrities,” Andy Warhol described the event in his diaries. “We rode in a limo out to Malibu and when we saw helicopters in the distance we knew we were at the wedding. Somebody had tipped the reporters off about where the wedding was and about ten helicopters were hovering, it was like ‘Apocalypse Now,’” the late artist, who was a friend of Madonna, wrote.

Among the celebrity guests was Cher, who attended the event accompanied by film producer Joshua Donen, her boyfriend at the time. The singer wore voluminous purple spiky hair that became a signature of the 1980s punk rock fashion. Her outfit also included a black power blazer with bold shoulders, layered over a lacy top and accessorized with a diamond-embellished cross brooch.

Tom Cruise, who was a year away from releasing “Top Gun,” paired his boxy cut blazer with a shirt featuring a gold geometric pattern — a trend that carried through the 1990s. Christopher Walken, Martin Sheen and Crispin Glover all embraced similar silhouettes with more conservative button-down choices.

Contrary to the cardinal rule of wedding etiquette, some of the female guests did attend the ceremony in all-white outfits, like Rosanna Arquette and Diane Keaton. The latter’s outfit featured a high-necked white top or turtleneck layered with multiple chunky gold chain necklaces, completed with a flowing white coat that created a quintessential 1980s look.

The wedding, which also marked Maddona’s 27th birthday, was held at real‑estate developer Dan Unger’s mansion above the bluffs of Point Dume. The singer wore a dress designed by Marlene Stewart, who was the costume designer of her “Like a Virgin” tour.

The gown, sold for $60,000 in 2014 by Julien’s Auction, featured a strapless bodice with a sweetheart neckline, ruched tulle with pink metallic mesh, and handmade ombré blossoms with gold bullion and beadwork. Accompanying the gown was a black bowler hat with a tulle veil and imitation pearl details, along with custom ivory silk brocade wedding shoes embellished with gold and silver appliqué, pearls, glass teardrops, and a petal pink rose bud by Di Fabrizio of Los Angeles. Penn was dressed in Gianni Versace.

Madonna and Penn were married until 1989.