For years, Diddy’s lavish White Party ruled Labor Day. Here are some of the most unforgettable celebrity fashion moments.

It has been 25 years since Diddy threw the first White Party in the Hamptons, an event that brought together an unmatched collection of A-listers for a culture-defining event.

·Reporter

September 4, 2023 at 9:00 PM·5 min read

Fifteen years ago, Diddy held the first White Party. For more than a decade, the event attracted A-listers who celebrated hip-hop, community and the evolution of culture. (Getty Images)

When it comes to era-defining soirées, few rival Diddy's lavish White Parties. For more than a decade, from 1998 to 2009, the annual extravaganza over the Labor Day holiday was pop culture's hottest ticket, with an unmatched guest list delivering indelible fashion moments.

"I remember the first party he threw in the Hamptons," Paris Hilton recalled to The Hollywood Reporter in 2008. "It was iconic and everyone was there."

In the early aughts, an invite to the exclusive bash solidified one's A-list status stretching across entertainment, business, finance, fashion and technology. Recurring guests included the Kardashians, the Hilton sisters, Leonardo DiCaprio, Jay-Z, Beyoncé, Mariah Carey, Mary J. Blige, Al Sharpton and Martha Stewart.

Designer Donna Karan, Tommy Lee, Mariah Carey, Diddy, Star Jones and rapper Rev. Run at the 2007 White Party. (Bryan Bedder/CP/Getty Images for CP) — Designer Donna Karan, Tommy Lee, Mariah Carey, Diddy, Star Jones and Rev Run at the 2007 White Party. (Bryan Bedder/CP/Getty Images for CP)

It has been 25 years since Diddy's first White Party, which was held Sept. 7, 1998, over Labor Day weekend.

The annual tradition began when Sean Combs (currently known as Diddy but variously known as Puffy, Puff Daddy and P. Diddy over the years) decided to showcase his new Hamptons homestead by inviting more than 200 gliteratti to a barbecue. That first fete featured a largely old-money and predominantly white crowd, and the media was quick to label the rapper a “modern-day Gatsby,” which he seemed to relish during a 2001 interview with The Independent in which he boasted, “I am the Great Gatsby.”

Truth be told, Diddy was far from F. Scott Fitzgerald’s Gatsby, who threw extravagant parties to impress his monied neighbors. In this case, it was the establishment that wanted a glimpse of Diddy’s world.

As the rap mogul told Oprah in a 2006 interview, the intention behind the first White Party was to integrate hip-hop into the echelons of the mega-rich, to find an intersection of both worlds for the sake of unity.

“I wanted to strip away everyone's image and put us all in the same color, and on the same level,” he told Oprah of that inaugural Labor Day bash. “I had the craziest mix: some of my boys from Harlem; Leonardo DiCaprio, after he'd just finished Titanic. I had socialites there and relatives from down south. There were 200 people sitting out here, just having a down-home cookout."

Diddy and Kim Porter with their twin daughters, D'Lila Star Combs and Jessie James Combs. (Mat Szwajkos/CP/Getty Images for CP) — Diddy and Kim Porter pose with their twin daughters, D'Lila Star Combs and Jessie James Combs. (Mat Szwajkos/CP/Getty Images for CP)

Mission accomplished, according to some cultural observers, who believe Diddy's parties changed hip-hop, and American culture, forever.

Over the years, the White Parties branched out from the Hamptons to Los Angeles and Saint-Tropez, and also included several Fourth of July iterations. The events also served as a major fundraiser for various international charities.

The last official White Party took place in Los Angeles in 2009, marking the end of an incredible era. Here's a look back at some of the seminal moments.