Inside Esquire and Ralph Lauren's Intimate Milan Fashion Week Dinner

It’s Fashion Week in Milan, where on Sunday night two iconic American brands—Esquire and Ralph Lauren—teamed up for an intimate dinner with friends at Palazzo Ralph Lauren (in other words: Ralph’s fabulous mansion in the heart of Italy’s fashion capital). Earlier in the day, the Palazzo welcomed fashion editors, buyers, and clients to see the brand’s
spring ’25 Purple Label collection, which was characteristically elegant, timeless, and chic. At the dinner–which began with cocktails around one of Ralph’s cars, a midnight blue Aston Martin from the ’60s (bella!)–guests included Hollywood luminaries Chris Pine and Colman Domingo, R&B superstar Usher, musical polymath Rufus Wainwright, Ralph Lauren Men’s Creative Director John Wrazej, Esquire editors from around the world, and more. At the end of the evening, Wainwright got up and performed several songs, including a duet with surprise guest John Legend. The duo teamed up to perform Mack the Knife (molto bello!). It was a memorable night. Check out photos from the dinner here.

Benvenuti in italia! It’s Men’s Fashion Week in Milan, where on Sunday night two iconic American brands—Esquire and Ralph Lauren—teamed up for a relaxed dinner with friends at Palazzo Ralph Lauren (in other words: Ralph’s fabulous mansion in the heart of Italy’s fashion capital). Earlier in the day, the Palazzo welcomed fashion editors, buyers, and clients to see the brand’s spring 2025 Purple Label collection, which was characteristically elegant, timeless, and chic. At the dinner—which began with cocktails around one of Ralph’s cars, a midnight blue Aston Martin from the early ’60s (che bella!)—guests included Hollywood luminaries Chris Pine and Colman Domingo, R&B superstar Usher, musical polymath Rufus Wainwright, Ralph Lauren Men’s Creative Director John Wrazej, Esquire editors from around the world, and many a friend in the wide world of menswear. At the end of the evening, Wainwright got up and performed several songs, including a duet with surprise guest John Legend. The duo teamed up to perform Mack the Knife. Memorable? Check. Fashionable? Double check. Fun as hell? Triple check. Take a look at everything that went down right here.