Vibe:A fancy library, where the best thing to read is the immense leather-bound cocktail list
Cozy factor:The two-story bar is mammoth, but the velvet-bedecked upstairs lounge has an abundance of warmly lit, tryst-worthy nooks, alcoves, and armchairs—plus two fireplaces.
Best sip:The autumn-toned concoction of Scotch and apple brandy aptly named Fall Be Kind ($13)
Vibe:Your granddad’s favorite dive
Cozy factor:To step into this narrow 80-plus-year-old watering hole on a frigid afternoon before the evening crowds hit is to enter a special kind of happy place. Find a spot at the end of the bar near the window, and watch the snow fly.
Best sip:A warming mug of glögg ($6), which the owners brew from scratch in a large kettle in the back
Vibe:A ’70s basement rec room for grownups
Cozy factor:The low-ceilinged subterranean space is appointed with just the right amount of kitsch—taxidermied swordfish, pleather captain’s chairs—though the bustle of patrons crowding the bar as they wait for tables at Dusek’s upstairs can be a mood breaker.
Best sip:A shareable bowl of cognac-spiked milk punch ($66 per bowl), which tastes like liquefied lemon meringue pie
Vibe:A chic downtown hideaway where the ’80s never died
Cozy factor:At this wood-paneled den on the seventh floor of the palatial Four Seasons, sculptural high-backed alcove seats are accented by zebra-print pillows and sleek photos of bejeweled ladies and animals. Sink into an armchair beneath Lady in a Choker and Black Swan and enjoy a bowl of housemade Cheez-Its.
Best sip:The full-flavored chocolate-orange rye old fashioned ($15)
Vibe:An old-time London pub that crash-landed on Western Avenue
Cozy factor:A fireplace, worn Persian rugs, damask wallpaper, and polished-brass bar fittings complete the throwback picture. And what could be more comforting than settling into a leather-backed seat with a beer and a killer burger?
Best sip:A pint of hand-pulled cask ale, like Maplewood Fat Pug milk stout ($7)