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I like to think the best way to stay ‘in the know’ is to split your time between highbrow establishments and lesser-publicized informal spots that attract a more youthful crowd. This applies in all aspects of life—you should be able to walk out the door in Public School and a Tom Ford suit in the same day. Being able to adapt to any crowd makes you socially invincible.

So, where am I sending the uptown crew that wants to venture out to the cool new downtown spot? Recently it’s been The Leadbelly, a new oyster bar and nightlife spot in the Lower East Side, NYC, from Ben Towill and Phil Winser, who staked their claim on the block with the Fat Radish restaurant in 2011. The Leadbelly is just a few doors down with a similar décor—homey and comfortable, like a downtown living room complete with mid-century furniture, vintage suitcases accessorizing the walls and bookshelves stocked with records.While the oysters and bar food are delicious, the drinks alone are worth the trek.

The seasonal menu is designed by mixologist Colin Asare-Appiah, who you may recognize from summers at Ruschmeyers in Montauk. While you’re sippin’ on a toasted almond white Russian, the scene around you will likely be a mix of extremely good looking 20 and 30-somethings from the area, but also sprinkled with some interesting characters associated with the Fat Radish crew—downtown nightlife fixtures, editors, musicians, fashion designers.

Expect a a low-key but scene-y evening and of course, the music which gets progressively more dance worthy after 10pm. If you come by on a Thursday, I’ll be sure to serenade you to with my favorite Reggae tunes throughout the night.

On the other end of the spectrum for those nights when you just want to feel sophisticated and cultured, check out my new favorite spot in Chicago, the Public Hotel.

Brought to the windy city by Ian Schrager, who brought us Studio 54 and Palladium, the Public Hotel is a makeover of the legendary Ambassador East Hotel, which drew truly glamorous frequenters like Frank Sinatra, Natalie Wood and Judy Garland. Schrager has preserved the name and cool factor of the famous Pump Room dining area that attracted such attention in the hotel. He even preserved Sinatra’s seat of choice – Booth One. But the new Pump Room is helmed by Jean-Georges who has reinvented some of the classic menu offerings from the original restaurant and added some of his own items comparable to his ABC Kitchen in Manhattan.

The bar scene is dim-lit but dramatic, full of the wealthy locals with swagger. And while the new décor is sleek and modern—and you’re no longer required to wear a jacket to get in—there is still an aura of the glory days. Just sidle up to the bar, order an Old Fashioned and feel it for yourself.

Best of all, after a few (three…four…?) of those, you can always just stumble upstairs to the hotel’s Frank Sinatra suite for a good night’s sleep. With its view overlooking Chicago’s Gold Coast neighborhood and out onto Lake Michigan, it’s enough to make ‘Ol Blue Eyes a little envious.