They say it’s the city that never sleeps. What to see—and what to wear—around the clock.
At the South Street Seaport, the backdrop is the Brooklyn Bridge in all its Gothic glory. Tulle top and wool skirt by Carolina Herrera; nylon tights, Hue; patent-leather shoes, Stuart Weitzman; leather bag, Cartier; 18-karat-gold bangles, David Yurman; camera, Canon.
Board the New York Water Taxi (212/742-1969; nywatertaxi.com; one-day pass $20) for a Fall Foliage Cruise ($35; 4½ hours) up the Hudson Valley, or hop on and off at 12 stops around Manhattan, Queens, and Brooklyn. Wool flannel coat by Derek Lam; merino sweater, TSE; jeans, 7 for all Mankind; stretch lambskin-and-patent boots, Chanel; patent-leather tote, Tods; leather belt, Etro; acetate sunglasses, Givenchy; 18-karat-gold hoops, David Yurman.
At the Neue Galerie (1048 Fifth Ave.; 212/628-6200; neuegalerie.org), stop by Café Sabarsky (212/288-0665; lunch for two $67) for Viennese strudel with schlag, then browse the museum's latest exhibition, on Austrian painter Gustav Klimt (October 18–June 30). Fedora Jersey dress by Diane von Furstenberg; pony flats, Aldo; cowskin suitcase, Hermès; bronze chain bracelet, Stephen Dweck.
The retro-hip Florent (69 Gansevoort St.; 212/989-5779; dinner for two $70), in the Meatpacking District, reflects the energy of the neighborhood—it's open 24 hours a day, great for a late-night steak frites. Jacquard shirt, skirt, and patent-leather pumps by Miu Miu.
The Private Roof Club, for guests and members only, at the Gramercy Park Hotel (2 Lexington Ave.; 212/920-3300; gramercyparkhotel.com; doubles from $545) is the perfect place to see and be seen while taking in art by Julian Schnabel and Damien Hirst. Silk radzmir dress by Dior by John Galliano; patent-leather heels, Stuart Weitzman; leather clutch, Louis Vuitton; 18-karat-gold and mother-of-pearl necklace and 18-karat-gold watch with mother-of-pearl face, diamond case, and leather strap, Van Cleef & Arpels.
Just behind the New York Public Library is Bryant Park (Fifth Ave. and 42nd St.), a respite from the hustle of midtown. A cup of morning coffee from 'Wichcraft (212/780-0577), a kiosk on the northwest corner, is $2. People-watching is free. Silk-wool–blend jacket and skirt by Alberta Ferretti; nylon tights, DKNY; leather oxford boots, Stuart Weitzman; leather duffel, Ghurka; bronze necklace with honeycomb links, Stephen Dweck.