Comme Des Garçons.   (Photo: Courtesy of Comme Des Garçons)

Day Four: Chelsea and the Meatpacking District
Push the envelope by scoping out the avant-garde fashions of these two adjoining neighborhoods.

10:30 a.m.: Jump-start your morning. Take the C or E train to 23rd Street for a caffeinated jolt at Café Grumpy. (They brew their coffee with an $11,000 Clover machine.) Nosh on a pumpkin-apple-walnut muffin from Brooklyn’s Blue Sky Bakery. You’ll be walking it off soon enough.

11 a.m.: Admire the architecture of apparel. Stroll down to 22nd Street then pass through the huge pivoting door and jagged aluminum tunnel into the cavernous home of Comme Des Garçons. You’ll probably be one of the few shoppers, since Rei Kawakubo’s abstract designs aren’t that well known, but the artsy shop clerks and risk-taking garments provide plenty of entertainment.

Noon: Buy a next-century bag. A few steps west is the futuristically gritty Balenciaga flagship designed by French artist Dominique Gonzalez-Foerster, who left the former garage’s cold cement floors intact. A glowing ceiling subtly changes from daylight to dusk, cloudy to sunny, fall to spring, while iceberglike structures display world-famous handbags.

1 p.m.: Belly up to the bistro. Point south to Gansevoort Street for lunch at 5 Ninth, a low-key alternative to nearby Pastis. The quaint townhouse exterior of this New American meatpacking staple houses a lovely back garden, intimate interior seating, and French flavors.

3 p.m.: Fancify your footwear. No New York shopping trip is complete without a stop at Jeffrey New York, just a few blocks up 14th Street. It's one of just two Jeffreys in the country, and the massive shoe collection is expertly edited, but keep your eyes peeled for the latest from Miu Miu and Chanel.

5 p.m.: Reacquaint yourself with classic DVF. At the intersection of 14th and Washington streets, you’ll find fashion legend Diane Von Furstenberg’s airy shop. The décor, like much of the clothes, is inspired by seventies glam. Take a load off on a bright-pink couch then watch as a friend tries on a signature wrap dress.

8 p.m.: Show off your swag at a blowout dinner. La Bottega, the balconied restaurant in the Maritime Hotel, is as super-stylish as your purchases. After a dinner of wood-fired pizzas and antipasti, take the party downstairs to Hiro Ballroom, a magnet for downtown rockers.