When Frank Sinatra was a fixture in New York’s nightlife, 52nd Street was still Swing Street, and cool was defined by the Stork Club and El Morocco. Well, even though saloons and elegant nightclubs no longer dominate, and it’s harder to find a piano player working through the Great American Songbook, Sinatra's style is still very much alive in New York, New York.

Some of his actual haunts are still cooking: you can still mangia bene at his beloved Patsy’s Italian Restaurant, and enjoy a cocktail at The Mulberry Street Bar, which Sinatra first patronized in 1941, while playing his music on the jukebox. You can still get great pizza at his favorite spot, Grimaldi’s under the Brooklyn Bridge, and PJ Clarke’s and 21 still serve a taste of days gone by. But there are also newer places that are classy classics. Even though 4 a.m. last calls have recently been threatened with extinction, there are plenty of spots where Sinatra’s style lives on, and where Sinatra would feel right at home.

The Campbell Apartment
A magical 13th-century Florentine hideaway just steps away from one of world’s busiest landmarks, this luxurious bar tucked into Grand Central Station served as an office for over three decades, then spent 40 years used for everything from a jail to a storage space. Today the decor is romantic, the bar is swank, and the crowd is swell (the dress code bans jeans and sneakers).

The Flatiron Lounge
This retro-style place—with its 30-foot long Art Deco bar salvaged from the fabled Manhattan Ballroom, banquettes, dark wood, and ironwork—specializes in Sinatra-era cool. One of its cocktail menus is dubbed “Flights Back in Time,” with Rat Pack-era favorites like the Sazerac, the Sidecar, and the Aviation. (If you’d prefer to stick with Sinatra’s drink of choice, Jack Daniel’s, they’ve got that, too.)

Brandy Library
The Brandy Library exemplifies the kind of unsnobby stylishness that Sinatra cherished. 900 Bottles of Cognac on the wall—so many they have to be fetched by ladder. 100 cocktails on the bible-thick menu. Leather chairs, a coat-check girl, a piano by the fireplace, jazz on the iPod—and live Sundays and Mondays.

Feinstein’s at the Loew’s Regency
Back in the day, every hotel had its nightclub and people dressed up to enjoy cabaret performers. Thanks to singer/pianist Michael Feinstein, there’s just such a primo spot today. Feinstein’s, a sleek supper club in the showbiz-friendly Regency, books the best cabaret acts from pop, jazz, and Broadway. As an acquaintance and admirer of Feinstein’s, Sinatra might join them onstage if he were still here.

Schiller’s Liquor Bar
Hip without being flashy, this noisy tiled bistro is all about atmosphere. The low-ceilinged corner former drugstore is packed nightly with a downtown mix of eye candy and well-dressed bohemians. The specialty cocktails include the locally dubbed “Delancey.” The elbow-to-elbow intimacy means nobody gets special treatment. And while Sinatra went for the more expensive vino himself, he would approve of the wine list categories: “cheap,” “decent,” and “good.”

Brooklyn Social
This joint was a former Sicilian men's social club called Riposto, and preserves its gorgeous Art Deco interior and sepia-tinted pictures on the wall. But as the sign on the door proclaims: “Non-Members Welcome.” There’s a garden, a pool table, and an eclectic jukebox, and the bartenders wear ties and mix mean martinis (and Old Fashioneds).

The Carnegie Club
Don’t worry—it’s not an actual private club. (Sinatra didn’t like those.) A block away from Patsy’s, this sophisticated cocktail and smoking lounge features live jazz three nights a week on a patch of floorspace downstairs beneath cathedral-like windows, including an actual Sinatra tribute every Saturday night—vocalist Cary Hoffman fronts an 11-piece orchestra (cover charge).

Hudson Bar & Books
Though it looks like a library, the books are mostly for show. (After all, Sinatra may have been an avid reader, but not when he was out on the town.) What’s for real are the single-malt Scotches, Bourbons, Cognac, and Armagnac, the tin ceiling and the copper bar top. Smoking is permitted, a welcome concession for those who, like Sinatra, can’t help themselves from time to time. And the live jazz on weekends and mixed-age crowd would suit him just fine.

The Lenox Lounge
No map of Sinatra’s New York would be complete without a stop in Harlem. The Lenox, opened in 1939 and restored to mint condition in 1999, in its heyday hosted performers like Billie Holliday and Miles Davis. Jazz still gets played, soul food gets served, and the crowd gets happy.