Shopping near the Empire State Building

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 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. 

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.

This sprawling culinary destination celebrates the food and wine of Italy’s 20 regions, with its market full of fresh pasta handmade while you watch a “pasta show,” hard-to-find specialties of salumi and formaggi, sustainable meat and seafood and bread made with a lievito madre sourced from Piemonte. If you’re looking for the perfect wine to pair with your meal, Eataly Vino’s two floors of Italian wine are just steps from the market. For those who want to learn even more, Eataly offers cooking classes that teach you how to make specialties like lasagna alla bolognese and limoncello tiramisu, as well as wine dinners with experts who will guide you through the history and traditions of the regions.  If shopping tends to work up your appetite, head to one of the 13 restaurants, bars, cafés, and counters throughout the 48,000-square-foot space. Sit down for a meal of Neapolitan pizza and a bottle of bold Chianti at La Pizza & La Pasta, or the catch of the day paired with a Grillo sourced from microclimates along the Italian coast at Il Pesce. For dessert, get a scoop of housemade gelato and babà al rum or bignès at La Pasticceria.

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.

Walking into this Flatiron spot feels as if you’ve just stumbled upon the best stall at the flea market. Worn-wood shelves support stack upon stack of assorted rainbow-colored dishes ($1–$17), mismatched vintage china ($5–$23), toile teapots ($15–$39) and other kitschy kitchenwares. The amazingly cheap price tags make it worth battling the often-pressing crowds to stock up on assorted flatware ($1–$6 each) and glassware, including oversize stemless martini glasses ($6), elegant champagne flutes ($8) and Italian-style painted wineglasses ($5). If you’re in need of a serious discount, plunder the sale section in the back for never-before-used castoffs from restaurant and hotel suppliers. But there are plenty of affordable, freshly minted kitchen goods too. Local-specific buys include platters printed with the Brooklyn skyline ($17–$25) and Floor Plan dinnerware (from $8 for a five-square-inch “studio” to $33 for a 12-by-16-inch “penthouse”).

There’s a rotating mix of astoundingly well-preserved designer and nonvintage clothing here, as well as one-of-a-kind housewares, shoes and accessories. We’ve found vintage Yves Saint Laurent blouses for $12, striped skinny ties for $6 and a pair of classic Salvatore Ferragamo pumps with bows on them for $10. Pretty much everything is a find, but you still get that thrill-of-the-hunt feeling.

Vogue photographs featuring the store’s antique garb line the walls at this living-history reservoir, where everything from 19th-century walking suits to neon Vivienne Westwood platforms is neatly arranged by era. Here you can rent a Chanel quilted suit ($1,025) or a Missoni knit dress ($895) for a fraction of the purchase price. Walk-ins are welcome, but it’s worth calling ahead to peruse the appointment-only upstairs area. There you’ll find a priceless ostrich-hemmed 1920s gold lamé gown by designer Charles Frederick Worth, a 1960s chain-link Paco Rabanne vest and Josephine Baker’s rhinestone-encrusted 1920s bra (recently rented by Lady Gaga). Pricing depends on the item and length of rental; there is a minimum fee of $200.

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).