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“We’re going to have a great event,” Jimmy Kimmel said, pausing for a beat. “As long as the tent doesn’t blow away.”

It wasn’t entirely out of the question. Said tent, the flimsy shield encasing the guests at Rihanna’s inaugural Diamond Ball, shook violently as the pre-storm bluster hit Los Angeles on Thursday night. As luck would have it, the night’s two biggest parties — the ball and Coach’s backstage bash — were held in venues that were far from weatherproof, with the former’s tent stationed at the top of a windy hilltop and the latter’s on the roof of a six-level parking garage.

This story first appeared in the December 15, 2014 issue of WWD. Subscribe Today.

Coach’s party at least started comfortably. It kicked off at the brand’s newly renovated Rodeo Drive boutique, where guests stayed warm and dry amid the plush carpeting and shearling chairs. As the cocktail party wound down, people began the half-block trek to the garage. Staffers handed out leopard-print scarves to guests as they exited the store. They came in handy once the rain started.

“I’ve never played on a parking structure before,” singer-songwriter Skylar Grey, the night’s opener, said. “It’s a cool event, quite the production.”

Grey probably didn’t mind since she didn’t really have to endure the elements. She and Kid Cudi, who also performed, spent most of the night in the greenroom backstage, while the rest of the guests attempted to stay dry under the eaves of a mile-long grilled-cheese bar and the plastic covering thrown up over the stage area. Kirsten Dunst arrived prepared, a scarf and umbrella stuffed into her tote. “Well, you know it’s about to rain,” she said. Still, she said she made the effort because “I really like Stuart [Vevers, Coach’s creative director], because, you know, I don’t normally come to these things. I don’t like to leave the Valley. It takes a lot to get me over the hill, I’m not going to lie,” she said.

On the other side of town, at The Vineyard Beverly Hills, guests of Rihanna’s were getting up their own hill. Kimmel, Brad Pitt, Ellen Pompeo, Ne-Yo, Kim Kardashian West, Kris Jenner, Salma Hayek and François-Henri Pinault made their way up a winding road from one checkpoint to the next, chauffeured in vans to the hilltop where the large, chandelier-filled tent stood overlooking a foggy and wet Los Angeles.

“I see you, Diamond Ball,” Rihanna purred into the microphone, greeting her guests. It’s the first annual fund-raising event for her charity, the Clara Lionel Foundation, which she founded in 2012. “It helps improve the quality of life not just for Barbados, but globally,” she explained later in the evening.

Bidders during the requisite live auction included Hayek, who bought a Damien Hirst piece for $190,000, and rapper Big Sean, who was outbid for a $39,000 Gucci package; there were also front-row VIP tickets to Kanye West’s yet-to-be announced tour next year, as well as a pair of his limited-edition, highly awaited Adidas sneakers, which went for $37,000.

Rihanna herself — sinuous in a blush-hued Zac Posen gown — also made her own donation via a performance. She brought the crowd to its feet with a set of her hits, including “Umbrella.”

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