Shopping near the Empire State Building

The iconic open-air Chelsea flea, brought back from the dead by the team behind  Smorgasburg and Brooklyn Flea, showcases 40 veteran vendors selling mostly historic collectibles. If you love eclectic costume jewelry, quirky furniture, midcentury art and ceramics, records, antiques and art, and more, you’ll spend hours combing for treasure here. Plus, you'll now be able to grab a rewarding snack on the way out from various Smorgasburg food vendors that will soon be revealed. 

MoSex’s recently overhauled gift shop is now twice the size (2,000 square feet) and double the pleasure. “We wanted the store to be a destination shop,” says creative director Mark Snyder. “We’re looking at products for their art, their design and their technology.” Such lofty merch includes the Dirty Flirty Novelty Company’s festive glass “pornaments” and Matteo Cibic’s functional fishbowl dildo.

The former home of the National Biscuit Company is a hot spot for foodies and shopping addicts alike. Primarily known for its wide-range of eateries, Chelsea Market is hands-down one of New York’s most notable food halls boasting more than 55 vendors (including Los Tacos No 1, Amy's Bread, and Miznon).  Whether you’ve got a hankering for a steaming-hot cup of seafood bisque, perfectly aged cheese or a strong and smooth shot of espresso, Chelsea Market has you covered. Aside from finger-lickin’ fare and sweet merchandise, the attraction offers historical charms such as the market’s iconic fountain, which was crafted using discarded drill bits and exposed pipe from the former Nabisco factory.

While the giant signs that adorn this department store with the label of “The World’s Largest Store” are not true anymore, there’s no doubt that the flagship Macy’s is massive (with a big history to boot). For over a century, New Yorkers and visitors from the world over have been visiting Macy’s at its iconic location at 34th Street and Broadway. Though originally founded as a dry goods emporium in the 19th century, today shoppers flock to the store's 2.2 million square feet—which takes up a whole city block—to buy clothes, accessories and home goods.As one of the few major brick-and-mortar shops specializing in mid-priced fashion left in New York in this age of online retail and luxury brand–palooza, Macy’s carries a large amount of designer names you recognize that won’t cost you premium prices—especially during the deeply discounted sales offered periodically throughout the year. The 63,000-square-foot shoe department is the biggest on the planet and carries everything from dress shoes and delicate stilettos to work boots and slippers. Last-minute gift shoppers might be overwhelmed by the sheer amount of options of perfumes, ties, scarves, watches and more, but great deals await those with patience.   Pro-tip: Look for the cool wooden escalators, which feel like stepping back in time.

Tucked between the Lincoln Tunnel and Port Authority bus ramps, this unlikely slice of city street is closed to traffic every weekend when dozens of vendors unfold their tables full of goods. Vendors tend to compensate for the out-of-the-way location by offering lower prices than found in the Chelsea lots, which makes it worth the trek. Be sure to hit Wildpalm Vintage for precious jewels and Store with No Walls for designer vintage from Oscar de la Renta and Versace ($10–$100).

Purple Passion has vibes, floggers and so much more in its 4,000-square-foot Chelsea store. Catering to couples, single women, pro dommes and men, it carries a huge selection of leather and BDSM gear, including halters, gags, corsets and strap-ons. Hot sellers include the Jack Rabbit buzzer, leather suspension cuffs and bondage rope. You can also peruse clothes, boots (up to size 15!), shoes, wigs and books—or sign up for any number of workshops. Most customers spend at least $10 on a single trip; the more adventurous will drop a few hundred.

This vintage mecca has been peddling men’s and women’s clothing and accessories since 1978, serving clientele as diverse as Alexa Chung, Marc Jacobs and Cyndi Lauper. Owner Laura Wills travels the world, scouting eclectic finds that span the 1950s to the 1990s, and organizes clothing racks by decade. Do you need sunglasses from the ’70s? How about a royal-wedding T-shirt from the 1980s? Head upstairs to check out higher-end specialty garments like men’s Moschino printed suit jackets ($595) and Hattie Carnegie satin cap-sleeve dresses with beading ($895). The boutique is transformed into a Halloween showcase for the month of October, and since the staff is made up almost entirely of stylists, it's a great place to put together a complete period look, including the era-appropriate wigs and accessories.

Since opening in Soho in 1993, Ina Bernstein’s minichain of designer consignment shops has expanded to six locations throughout NYC, including spots on the Upper East Side, in Nolita, Noho and now Chelsea. The spacious store is painted stark white to let the covetable preworn pieces—including Prada wool coats ($375–$625), a pair of Miu Miu leather boots ($250) and a Louis Vuitton leather mini logo purse ($595)—stand out on its well-edited racks and organized shelves. If you’re saddled with name-brand threads, make an appointment to unload your gently worn castoffs for up to 40 percent of the overall resale value. Keep an eye out for INA’s own eponymous house label of unisex basics that complement the higher-end merchandise, such as comfy cashmere beanies ($90), arm socks ($85) and fingerless gloves ($75).

This flower shop in the heart of the Flower District has many blooms to choose from at affordable prices. Some of the best sellers start at just $50, while some of the more expensive bouquets are still on the cheaper side at $70. This shop has different kinds of flowers for all different types of occasions like birthdays, anniversaries, baby showers and dates in NYC.

Right by Rockefeller Center, this posh Fifth Avenue department store is the place to go to for high-end retail and international luxury brands. Along with browsing through houseware, clothes and accessories, linger at in-store designer boutiques like Chanel and Louis Vuitton, its mecca shoe department or the beauty counter.