On Friday evening, masked guests gathered at New York’s Pierre Hotel for the annual Save Venice Ball. This year sponsored by Buccellati, Dolce & Gabbana, and Dolce & Gabbana Beauty, the evening was expectedly glamorous, with guests pairing elegant ball gowns and impeccable suits with everything from plastic masks to sky-high headpieces (though the majority of the evening’s crowd favored the latter). Following the theme of the night Il Piacere dell’Amore (The Pleasure of Love), the usual stylish suspects such as Karolina Kurkova, Julia Restoin Roitfeld, Jessica Hart, and the brothers Brant posed before a gilded heart-shaped centerpiece as they made their way into cocktail hour. Inside, the Pierre’s mirrored walls were put to good use by guests adjusting their masks, but as is the case every year, slipping headpieces were just the beginning of the costume conundrum. “My glasses didn’t work with this, so you’ll have to lead me to the bar,” said one man, as another desperately sought to deliver a drink to his unrecognizably masked wife. Board member Charles Tolbert playfully attempted to sip from his drink beneath a hand-made headpiece that completely covered his face as another partygoer lamented over the originality of his Phantom of the Opera-esque eyepiece. “They told me this was one of a kind, but I just saw three guys wearing it, so I’m feeling a bit cheated,” he said. Though the masks did what they could to hide the visages underneath, each wearer found a way to make the theme suit their occupational personalities: actresses Emmy Rossum and Allison Williams chose simple and pretty stick masks; man about town Di Mondo turned heads with a headpiece made of iPhones; designer Wes Gordon mixed Tom Ford with Party City; and tastemaker Sofia Sanchez Barrenechea de Betak adhered red rose petals to one of her eyes. The evening’s more extravagant ensembles competed for “Best Mask” honors, which ultimately went to Dr. Susan Krysiewicz (winner of last year’s Best Lady’s Mask) and Mr. Thomas Bell, and Eric Marx and Public School’s Maxwell Osborne, who wore animal-shaped helmets by the Brooklyn-based designer Maxwell Steiner. In a room filled with immaculate ensembles, it was difficult to tell whether the mask or the clothes were the most important. “The mask, of course,” declared Osborne—who was, for the record, wearing Public School.