Shopping near the Empire State Building

This used bookstore in Midtown is the NYC outlet of a Japanese chain, and the discounts are particularly deep—check out the selection of $1 books. The manga selection is extensive, and folks interested in learning Japanese can pick up a number of language books or simply immerse themselves in the culture via video games and movies from the island nation. Thrifty sorts can get an even bigger bargain by selling old books and obsolete CDs and DVDs. 

This charming Chelsea bookstore offers a strong selection of books in literary fiction, translation, art, photography, film, poetry, music, history, biography, natural history, science, and current affairs. Plus, it features books for children and young adults. Regular readings, signings and discussions, some featuring well-known writers, are further good reasons to drop by. Even betters? All readings are free, with no reserved seating; seating is limited and offered first-come, first-served. Check the shop's website for upcoming events.

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.

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. 

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.

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 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.

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.

It's cool to donate your old duds and furniture to Housing Works, so the shelter-oriented charity's thrift stores are among the city's best. The prices aren't the lowest, but the stock is quality. If you're lucky, you can score designer pieces (in clothes and furnishings) you'd never be able to afford new. You just have to do a little rummaging.