VIBE

Swish Art Deco hideaway where swing-era music can be faintly heard above the chatter of smartly dressed schmoozers. The posh crowd reclines on plush blue banquettes or perches atop velvet stools lining the restored mahogany bar (a relic from former Sinatra hangout The Ballroom). Partner Julie Reiner has shaped a menu of drinks inspired by the early days of cocktail craft that incorporates fresh fruits and homemade syrups; the drinks recall the age when fine ingredients were masterfully muddled to mask the flavors of bootleg booze (not that these high end spirits need any masking at all!).

WHAT WE WOULD WEAR

Though the lounge remains casual, we’d dress up for a night on the town here with a black tunic or dress, lacey leggings, chic boots, and some statement baubles.

GO HERE WITH

A group of single girlfriends; a date

CROWD

Singles and twosomes belly up to the bar, while well-dressed groups of 30- and 40-somethings settle into the banquettes after work.

WHY WE LIKE IT

It evokes the Prohibition-era vibe Manhattanites are so fond of, while (thanks to the fab cocktails) still remaining true to a hip and trendy drinking scene–and we love how eclectic the crowds are as a result. This is a great place to take fun-loving coworkers for an after-hours quaff, the girls for a catch up session, or even a date for the sexy surrounds.

WHAT WE WOULD CHANGE

It can get too crowded on weekends, making conversation a shouting match at times.

GOOD TO KNOW

The Flatiron Lounge is housed in a historic landmark building dating back to 1900. While classic New York is engrained in the building’s architecture and recreated in the dark wood and ironwork of the main floor, Flatiron Lounge also features a darker and clubbier downstairs space, where more modern touches like gold-leafed walls and current music appeal to trendier crowds. For those into quiet cocktailing, Mondays and Tuesdays (after the weekend rush) are the slowest nights of the week.

CLOSEST COMPS

Employees Only (New York); The Raines Law Room (New York)

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