Fendi   (Photo: Courtesy of Fendi)

Day Two: Midtown & Upper East Side
Though big department stores take up the most real estate on Fifth Avenue, the biggest trends are born at the flagships of famed designers.

9 a.m.: Drink (coffee) and run. Pop into ING for a quick caffeine boost. For a banking center, it’s surprisingly mod—and where else can the baristas rattle off interest rates? It's closed on weekends, however, so the Starbucks across the street will have to do.

10 a.m.: Pay homage to Donatella. Louis Vuitton? Christian Dior? It’s hard to know where to start your second day, but we vote Versace, the medusa-emblazoned landmark known for its sky-high heels and ostrich-leather bags. Head up to the womenswear department on the second floor to drool over va-va-voom dresses.

11 a.m.: Show some respect to Karl Lagerfeld, too. Walk one block north to Fendi, an enormous store with a cascading virtual fountain projected onto huge screens. The 7,500-square-foot space is as eye-catching and slick as the label’s metallic minidresses and slinky blouses.

11:45 a.m.: Lock your eyes on that interlocking G logo. Fendi’s next-door neighbor is none other than Gucci, where low-lighting, European trance music, and mazelike staircases will have you spinning. Don't miss the draping gowns or the men’s skinny trousers on the fourth and fifth floors respectively.

12:30 p.m.: Have an artful meal at MoMA. Take a much-needed break with lunch at the Modern, the upscale eatery at the Museum of Modern Art one block west. Torn between tuna tartare and roasted Maine lobster? The three-course prix fixe ($55) lets you have a little taste of everything.

2:30 p.m.: Resume the hunt at Bloomingdale's. It’s equality of the sexes at 59th Street and Third Avenue where guys can peruse the copious man-bag section or shelves of denim and women can swoon over an impeccable array of winter scarves on the first floor.

4 p.m.: Don’t be late for Tom Ford. Hail a cab to 70th Street since the new Tom Ford store closes at 5 p.m. (unusual for NYC). Like its hirsute namesake, this over-the-top men’s boutique oozes sultry masculinity, with shopgirls dressed as housekeepers, and a floor carpeted in beaver rugs.

5:15 p.m.: Get a rock with some history. Stroll down to 64th Street to peruse the fine jewelry at Demner (named by New York as the best vintage-jewelry shop of 2007). Unless you’re ready to fork over sums in the five-digit range, this may be a look-but-don’t-buy destination.

7:30 p.m.: Enjoy a hard-earned cocktail. End your wandering a few 6-train stops south at Bookmarks, the rooftop bar at the Library Hotel, near Grand Central Terminal. The bar’s extraordinary views and tongue-in-cheek cocktails like the Gin and the Giant Peach make for an excellent nighttime warm-up.