Toronto has many sophisticated people who want a sophisticated place to go. Enter the lounge, the place that warrants a high heeled pump or a Windsor knotted tie. Mind you, we have also included some establishments that wouldn't blink if you decide to make your entrance in yoga pants.
The word lounge already indicates the relaxed nature of the evening. Rather than working to scream over loud bass, you can converse. You have your choice of cocktails to either help along or hurt that conversation. Some lounges get opinionated on what your beverage of choice should be by specializing in tequila, such as the Reposado Tequila Bar. Others are more opinionated on what your beverage of choice shouldn't be, such as Hoof Cocktail Bar's obvious distain of vodka.
You can get a magnificent view of the city from many of these locations, whether you are peering over a rooftop or seeing Toronto from a new angle. The DEQ at Ritz Carlton Toronto has a magnificent patio that provides an urban oasis right in the heart of downtown. If downtown is your jam, you can always transition from the office to the tiki bar with Toronto's polynesian oasis, The Shameful Tiki Room.
Some of these locations are hard to get into and others require a membership. Are you serious enough about your cocktails to make that kind of commitment?