VIBE

Running parallel to the famed Fifth Avenue, Madison Avenue is comparable in both glam-factor and expense. This prized stretch of real estate is home to a long line of the highest-end boutiques and ultimate luxury designer labels, like Gucci, Prada, Tod’s, and Hermès, as well as niche and trendy labels like Fred Leighton, Tom Ford, Oliver Peoples, and Jimmy Choo. To walk it feels like taking a trip through a celebrity shopping mall, as you’ll very likely be rubbing shoulders with starlets and socialites along the way. It's a perfect destination for the ultimate spender or for those who enjoy upper-upscale window shopping.

USE A PURCHASE FROM HERE FOR

Red carpet appearance or brag-worthy event; wedding gift

WHY WE LIKE IT

Even if we’re not in the market to purchase anything, it’s worth a stroll down Madison for the window dressings alone. The flagship store of Barneys New York makes its home here and stocks a number of luxury labels (many with Madison Avenue boutiques of their own). The street plays host to some classy restaurants, too.

GOOD TO KNOW

Whereas Fifth Avenue tends to be touristy and crowded, given its location next to Central Park and the great museum attractions, Madison Avenue is much calmer and tends to be favored by the wealthy looking to shop at leisure while avoiding the crowds. If you want to take a shopping (or window shopping) break, we love the Vosges Chocolate store (at 83rd Street) for their exotic truffle collection–be sure to try Mo’s Bacon Bar.

CLOSEST COMPS

Fifth Avenue (New York); Rodeo Drive (Los Angeles); Bond Street (London); Avenue Georges V (Paris); Rue Saint-Honoré (Paris)

Click here for our full-form mobile travel guide, The Purple Passport to New York City.