Jon Hamm, Anna OsceolaPhoto: Mikey DeTemple

The skies were grey. Then moody. Then, miraculously, golden. As the clock struck five on Saturday evening, the clouds over Lake Montauk parted and the sun beamed down—just in time for Loro Piana’s chic cocktail gathering at the Crow’s Nest.

Among the first to arrive were Alexandra Daddario and Jon Hamm—two of the evening’s most star-studded guests. Daddario, dressed in a pale seafoam pleated skirt and soft white knit, made herself right at home at the backgammon table, diving into a match with a fellow guest as though it were the most glamorous tournament in town. Hamm, fresh off the news that his Apple TV+ series had been renewed, held court near one of the beachside lounge setups, trading stories and charming absolutely everyone within reach. His wife, Anna Osceola, stood nearby in a minimalist ivory dress and slouchy sweater, a study in coastal polish.

To toast the season (and subtly debut its Resort 2025 and new eyewear collections), Loro Piana transformed the lakefront stretch of sand into an elevated playground. Wicker lounges sat atop woven seagrass carpets, white-upholstered sofas flanked by the brand’s signature Art of Good Living touches—cashmere-lined backgammon sets and leather-trimmed Connect Four games artfully arranged for play.

Naturally, Loro Piana had dressed many of the evening’s guests, turning the crowd into a softly sunlit palette of beige, greige, and perfectly pleated linen. And when the sun made its theatrical entrance, the brand’s new sunglasses—gifted to attendees—ensured no one was left squinting.

As DJ Bec Adams spun a breezy set and spritzes were passed around, guests like Will Arnett, Cynthia Rowley, Carolyn Tate Angel, Iana Godnia, Casey Fremont, and Alejandra Alonso Rojas settled in to enjoy the scene. With the tide gently rolling in and the sky streaked pink and lavender, the evening captured what Loro Piana does best: quiet elegance with a sense of place.