SiliconValley royalty Kevin Systrom and Nicole Schuetz wed in California Wine Country.

"I feel like I have two good ideas per year, and this was one of them,” says Nicole Systrom. Though this is certainly not the case for the founder of clean-energy investment firm Sutro Energy Group, transforming her wedding to Instagram cofounder and CEO Kevin Systrom into a Jazz Age–themed black-tie masquerade ball in Napa was, unquestionably, a lightning-bolt moment. The October 31 nuptials featured one memorable idea after another, from the bride’s walk down the aisle to the tune of “Nobody Does It Better” to the band that played their daytime reception: a Wisconsin high school jazz group that the groom discovered on YouTube.

Following the alfresco ceremony and luncheon at the Beau- lieu Vineyard, the 180 guests returned to their hotel to discover the custom masks that had been delivered to their rooms in their absence—a subtle nod to Halloween that managed the tricky feat of adding an elegant playfulness to the proceedings without devolving into camp. (“We didn’t want anyone show- ing up in, say, a police costume,” said Nicole with a laugh.) For the evening’s party, the bride changed out of her floral ceremony dress (by Mark Zunino) into a pearl-and-sequin- embellished number (by Lihi Hod) with a twenties vibe. Donning masks, the couple led their family and friends to the tented dance floor, where they all remained for hours, sipping cocktails and snacking on—what else?—handmade Halloween candy. “We wanted to do something that people would remember forever,” said Nicole. #Success.