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. 

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”).

In 2003, Artists & Fleas first opened in Williamsburg, but thanks to owners Amy Abrams and Ronen Glimer, you can shop awesome vendors in Manhattan's Chelsea Market. Just like the original location, this version of Artists & Fleas features goods that run the gamut from art and design to fashion and vintage. There are more than 30 independent designers hawking their goods everyday, so stop by to check out our personal favorites such as menswear brand Curated Basics, baubles from Brooklyn Charm and ready-to-wear designs by Avalove.  

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.

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.

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.   

The years of tailoring experience that can be found at Alan David Custom is evident as soon as you walk through the unassuming midtown door and enter a room full of every kind of suit you could imagine. Once you settle into a comfortable leather chair surrounded by your many sartorial options, a friendly and helpful staffer will ask you questions on preferred color, pattern and type of fabric before presenting numerous materials from the likes of Loro Piana, Zegna, Reda, Scabal and more.  After making your choices for suit fabric and lining, an on-site tailor will take over 20 precise measurements for a perfectly tailored garment. Custom suits and tuxedos start at $1,400 while overcoats start at $2,000 and dress shirts start at $220. The business promises full canvas bespoke construction, a guaranteed perfect fit and free alterations for a lifetime. Those customers interested in an additional level of tailoring can also choose to have a basted fitting for garments which adds about two-weeks of time and $100 to the suit. Alan David Horowitz, the current owner and CEO of Alan David Custom is a fourth-generation tailor—the business was originally founded by his great-grandfather who opened his first store in 1926 on the Lower East Side. All of the custom garments on offer here are hand-sewn in the New York shop as opposed to overseas production and average turnaround is 4-5 weeks with a 2-week rush program also available.

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.  

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).