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. 

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.

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.

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.

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.   

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.

In the heart of Flower District, this store offers a wide range of styles, from traditional to modern. The florists specialize in classy bouquets ($55–$75) like a fuchsia-hued arrangement of pink spray roses, Peruvian and Asiatic lilies, and mini carnations displayed in a crystal vase. Best part? This shop features same-day to all five boroughs (delivery prices may vary).

The long-running New York institution’s flagship store, Academy Records and CDs—next door to the tiny niche where it originated back in ’77—boasts the city’s best selection of used classical CDs and LPs, plus an impressive array of rock and jazz discs. (The store is connected in name to NYC's other two Academy Record locations, though those spots focus mainly on vinyl). Approachable help and knowledgeable buyers add to the overall experience. Plan to spend time—and money—at both locations.  

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.

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.