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.
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