It began as a social experiment: Could San Francisco support an exclusive, New York-style black-tie charity event catering to a carefully vetted thirtysomething set? Would there be enough people, and if there were, would they show up and would it be cool?

Judging from the Legion of Honor's inaugural Midwinter Gala—tied to the opening of the Art Deco show at the museum—the answer is yes. Three hundred and forty guests, almost all under 45, good-looking, and drawn from the city's socially prominent or affluent (or both) families, showed up for the fete, which, according to ringleader Trevor Traina, was modeled partly after the Museum of the City of New York's gala.

"Many people don't realize how many interesting, attractive, and stylish people we have here in San Francisco, and I think we've shown that tonight," Traina told the Socialist.

Well, sometimes being discerning (cynics call it a euphemism for shallow) helps. While it wasn't exactly on the level of a New York gala—the ambition, a vanity fair of Oscar, Carolina, Dior, Valentino—most in attendance agreed it was a good start. Many guests made serious efforts to get decked out, if not in Deco as the invitation suggested, at least in swank attire, making the event among the most fashionable by local standards. There were the classicists: Vanessa Getty came in a high-voltage shimmering Dior gown and diamond Deco earrings, Victoria Traina in a Narciso Rodriguez gown with a white fur stole, and Tamara Winn in Oscar de la Renta, and San Francisco's own style director, Kathryn Retzer, wore a rust-colored Carolina Herrera gown with an undulating train. They were joined by the trendier types, such as Samantha Traina, in a Proenza Schouler gown, and Kimberly Bini, who wore Ungaro. And, of course, there were a few period people: Dorka Keehn in a yellow flapper dress with feathered headpiece, and Tatiana Sorokko in a 1927 Jean Patou couture dress. Friends from out of town such as Lisa Firestone, Kelley Johnson, and James Zemaitis of Sotheby's swooped in on the event. Zemaitis, who specializes in 20th-century design, was amused to discover one of his pieces, which he had donated to London's Victoria and Albert Museum, on display.

The event felt more like a private party—even a chic prom or reunion—than a big public blowout, simply because virtually everyone in the room seemed to be closely connected. To the party's credit, a few different cliques of the junior set were represented. The roster ranged from Andre de Baubigny, Carlo Mondavi, and Jennifer and Doug Biederbeck to Summer Walker and Vanessa Carlton.

There was an air of Fast Times at Trevor and Vanessa High as the two cochairs became the head boy and head girl at the party. The tables were placed concentrically around their two tables, and it was clear, as it is at a fashion show, that you are where you are seated. Wine came courtesy of Trevor's current girlfriend, Alexis Swanson (of Swanson Vineyards), and at least a few guests that night joked, "Would you like some more Alexis?" while sipping it. And the cool kids, of course, were the ones who loitered in the smoking area at the entrance to the museum. The space became almost the VIP lounge, a refuge from the impersonal, cavernous courtyard and the band.

Most seemed to have fun that evening. Guests even did a train on the dance floor, their faces betraying careful concentration as the band played covers of '80s hits. For some, that was a depressing footnote—"That's, like, for bar mitzvahs," said one partygoer. But for many, the notable flaw was a buffet-style dinner at an ostensibly high-tone function. Perhaps that meant there would be more money left to benefit the museum, which would explain why Traina repeatedly asserted the gala would be among the museum's most profitable.

Two weeks prior, the Legion of Honor had been on the social hit list when it hosted the Bouquets to Art flower show. The party's star was Jeff Leatham, a young, Gucci-clad floral designer visiting from his post at Paris's George V hotel. The model turned floral sculptor was hosted by Denise Hale earlier in the day at a lunch for 24 at Postrio. Among those present were California's former first lady, Sharon Davis, and friend Sofia Tsakopoulous (of the Sacramento real estate family), Wilkes Bashford, and journalist P.J. Corkery.

It must have been a busy week for the socialholic Hale, who only a few days before had hosted a lunch at Farallon for New York GOPer Georgette Mosbacher, who overtook the usual anodyne lunch conversation with serious political discussion—even debating the Socialist on Mayor Newsom's decision to issue gay marriage licenses. "It's not a civil-rights issue," she said unabashedly, knowing that she was in what lunch guest Legion of Honor curator Robert Johnson said was "Injun" territory for a conservative GOPer. Still, she enjoyed herself, joking with the Socialist on her way out that "at least we didn't just talk about decorating or where we're going on vacation next." And as if that wasn't enough for Hale, she also appeared at a dinner for Leatham given by hairstylist Alex Chases, who rounded up a roster of the city's social gay men plus La Hale at his Nob Hill apartment.

The day before Chases' dinner, his next-door neighbors John Wright and Marsha Monro Wright (they share a terrace at their ninth-floor apartments atop Nob Hill) invited the opera crew, including Marilyn Timoney and Athena Blackburn, to meet James Ferragamo, an executive for his family's shoe empire. Ferragamo was in town on a global business tour and dropped by Una Bella Serata, the opera event his company sponsored. Although he spoke impeccable English, the dapper young man didn't need to say much before the ladies present swooned. Now who said it was bad to be shallow?