Over Memorial Day Weekend, A Great Gatsby-Themed Bash Ushered in the Next Roaring ’20s 

An inclement weather forecast couldn’t keep a group of well-heeled revelers from tearing up the dance floor on Saturday night in Sagaponack, though it was cleverly referred to throughout the evening as West Egg.

With nods to the beloved F. Scott Fitzgerald novel and its many film adaptations, The Great Gatsby came to life in spectacular fashion this past weekend, orchestrated by Cinema Society founder Andrew Saffir and his partner, luxury marketing guru Daniel Benedict. While the celebration marked Benedict’s birthday, it also signaled a return to some level of normality, or perhaps a new roaring ’20s. “There is definitely an element of getting your sea legs back socially,” admitted Carla Gugino, whose tuxedo and tails were a fitting homage to silver screen starlets like Marlene Dietrich and Louise Brooks. “The nice thing is that everybody seems to be feeling that, after so many months of deciding between your daytime and your nighttime pajamas!” 

Those who made the trek from town to country for the occasion—Brooke Shields, Gayle King, and Mariska Hargitay—were greeted at the seaside home with a 1929 Studebaker sourced from a film production company, and a healthy supply of cocktails named after Gatsby characters. The Daisy Buchanan quickly became a crowd favorite as a troupe of Buchanan-inspired looks strolled into the room. For Zosia Mamet, the evening’s look included a fur stole and a blonde bob wig, while Dylan Lauren, known for her rainbow-hued ensembles, opted instead for a dazzling black sleeveless halter top sweater lined with silver crystals—it was designed by her father, naturally, and she dressed it with a vintage chocker repurposed as a headpiece. Though it was Katie Couric’s flapper-inspired headpiece that truly did turn heads. “I really wanted one of those little felt cloche hats, but that looked a bit too daytime, so I saw something that looked very roaring twenties on Etsy,” Couric, in Carmen Marc Valvo, told Vogue. “It was $38, and I thought I’d splurge.”

Following cocktail hour, dinner unfolded under a soaring tent with Art Deco-inflected decor, but before anyone had a chance to tuck into the evening’s first course of caviar and Champagne, Benedict rallied the crowd. “All I wanted to do is have a little dance party,” he said. “So you need to hit the dance floor now to get the party rocking.” 

The ensuing playlist of feel-good singalongs, spun by William Grand, was just what the doctor ordered. Drew Barrymore, in a voluminous black Valentino gown and newsboy cap, became the star of a dance circle populated by Jane Krakowski, Christie Brinkley, and Jill and Harry Kargman. Donna Karan, meanwhile, spun her feather boa around, catching and delighting her fellow dancers. “I have never seen everyone jump to the dance floor to dance to George Michael like this before,” Jennifer Esposito, in a vintage Jean Paul Gautier pinstripe jumpsuit, told us. “It was pure release.”