Versace.   (Photo: Shanna Ravindra)

Day Two: Midtown and the 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 Capital One 360 Café for a quick caffeine boost. For a banking center, it’s surprisingly modest—and where else can the baristas rattle off interest rates? If Starbucks is more your game, there’s one around the corner on 57th Street.

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 five blocks north to Fendi, an enormous store designed by Peter Marino that’s framed in dazzling white Italian limestone. The 4,000-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. Around the corner from Fendi is none other than Gucci, where low lighting, European trance music, and mazelike staircases will have you spinning. Don't miss the men’s skinny trousers or the draping gowns on the second and third 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 marinated lobster and pistachio-stuffed chicken? The prix fixe ($66 for three courses, $76 for four) 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 the comprehensive beauty department on the first floor.

4 p.m.: Don’t be late for Tom Ford. Hail a cab to 70th Street, since the Tom Ford store closes at 6:30 p.m., which is unusual for NYC. Like its hirsute namesake, this over-the-top men’s boutique oozes sultry masculinity.

5:15 p.m.: Get a rock with some history. Stroll down to 64th Street to peruse the offerings at Chanel Fine Jewelry, where some of the designs are still based on Coco Chanel's original sketches. 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 Tequila Mockingbird make for an excellent nighttime warm-up.