Girls night out! This weekend in New York City, famous friends Taylor Swift and Selena Gomez linked up to have dinner together at Monkey Bar. (A chic choice, if we say so ourselves.) Instead of hitting up some of Swift’s favorite downtown hotspots like Via Carota or The Corner Store, the duo headed uptown for a more old-school glamorous vibe. And, naturally, they had the fashions to match: They totally perfected the art of an Upper East Side outfit.

You know the kind of uptown wardrobe we’re talking about here: That monied, quietly-luxurious style that you’ve seen Lily Van der Woodsen wear on Gossip Girl. Swift and Gomez embodied the Upper East Side look by choosing pieces that were classic and timeless—and expensive looking. Swift wore a black crepe Gucci two-piece set, including a tank and skirt with sequined trim. She paired it with metallic platforms for more of a going-out feel. Gomez, meanwhile, leaned into neutrals with a tonal look: The Only Murders in the Building star wore a khaki suit from Ulla Johnson’s fall 2025 collection with a brown halter top, her blazer slung over her shoulder like a true boss. On her feet, gold slingback pumps from Larroude.