Let The Games Begin! Stars Rang in the Milan Winter Olympics at Ralph Lauren Palazzo

UsherVittorio Zunino Celotto/Getty Images

Since 1999, Ralph Lauren Palazzo has stood regally on Milan’s Via S. Barnaba, with its Italianate stone and majestic columns and archways. Yet once inside, the venue is undeniably a tribute to the all-American charm the label is so synonymous with. That patriotic pride and spirit was amplified—five-rings-fold—this evening as the brand hosted a kickoff party for the Milano-Cortina Winter Olympic Games, which officially begin on Friday.

Since 2008, Ralph Lauren has outfitted Team USA with ceremony and off-duty wear, and this year, the collection is among its more thematically varied. There’s everything from leather aviator jackets—similar to the kind worn by Ralph himself when he started out selling ties in the late ‘60s—to snow-hued duffel coats. The latter was what Usher was wearing when he arrived, after being held up in traffic behind the Olympic flame.

David Lauren, chief branding and innovation officer, said the Ralph Lauren team is always struck by the “humility and understatement” of the Olympians they work with: “While they have to have a certain confidence, we’re always impressed by their focus, discipline, and training. With each athlete that we’ve met, we really feel they’re incredible representatives of America.”

In the palazzo’s atrium, guests including Maggie Rogers, Marisa Tomei, Benito Skinner, and Shaun White mingled while margaritas and Champagne were poured. Bowen Yang and Matt Rogers, comedians and hosts of the popular Las Culturistas podcast, could be overheard revealing their fantasy third and fourth bobsled teammates: Ashley and Mary-Kate Olsen. When asked what Games discipline they thought they’d excel at, they didn’t hesitate. “Ohhhh. We were talking about this before in the car! Speed-skating for him, as he grew up a track star,” Yang said, pointing to Rogers. “I think skiing for Bowen; I really do,” Rogers offered in return. “And I’d love to see you do the one where you launch yourself into the air. Ski-jumping. Because I think there’s something really glamorous about that. I would just love to see Bowen Yang fly.”

Moments later, Usher walked into the palazzo’s showroom–revealing a proper look at the sharp navy suit that had been underneath the aforementioned duffel. “First of all, I think curling could be fun,” he said, ruminating about what winter sport he’d switch careers for in a fictional life-swap scenario. “But, umm… I think snowboarding would be my fantasy.”

Downhill, or halfpipe?

“Halfpipe, for sure. And I’d have a great coach. It’d be Shaun White,” he concluded.