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’re one of the first New York cafés to brew coffee with the hi-tech, ergonomic Pour Steady machine.) Nosh on pastries from various Brooklyn bakeries (including vegan and gluten-free treats); 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: Browse chic, mid-priced womenswear. Wander a bit south to Rebecca Taylor's bare-brick boutique. The New Zealand native's cozy shop feels like a sanctuary for classically feminine clothes, stocking everything from silk A-line dresses to satin camisoles.

1 p.m.: Grab a burger. Head around the corner for lunch at Bill’s Bar and Burger, a low-key alternative to the Meatpacking District's high-end bistros. The juicy burgers are made from a custom Pat LaFrieda blend, and the casual dining room will let you recharge for the rest of your shopping day.

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 Jeffrey stores in the country, and the massive shoe collection is expertly edited. (But be sure to 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 1970s glam. Take a load off on a bright-pink couch and watch as a friend tries on a signature wrap dress.

8 p.m.: Show off your swag at a blowout dinner. The industrial-chic Monarch Room, located across the street from Chelsea Market, is as super-stylish as your purchases. Dine on eggplant toast and the spiced duck breast, and get some people watching in to boot.