For dinner you could do Jean-Georges Philadelphia. They do have a dress code although not as strict as jacket required. On the cocktail side of things you could try Hop Sing Laundromat. The owner has both a dress code and behavior rules so you won’t be in there with people in sportswear. Unfortunately, I can’t help you on the night club side of things.

Back in the day Le Bec-Fin would have been the restaurant for you. Required jackets, the servers wore tuxedos, and the place was pretty opulent. They closed after things got more casual and that type of dining went out of style.

I definitely read this as “upscale pizzas” at first…

Since you mentioned “opera,” Garces has a place in the Kimmel Center. That would be convenient if you wanted to catch dinner and a show.

edit: okay, I am just useless today. First pizzas, now I’m suggesting a place that closed a month or two ago… My other ideas might be a little “past their prime” too, but I’d look into Vedge, Zahav, Parc. In general, Starr, Garces, and Vetri are probably the biggest chefs that each have a number of higher end places in the city. Probably can’t go wrong at any of their higher end spots.

Here’s a list of Philly places that have been finalists or won James Beard awards but that does not mean they are all high end and you’d probably be out of place in a suit in many of them.

edit: in terms of other entertainment, the Philadelphia Orchestra is a top-tier orchestra. If you want a free option, Curtis has recitals open to the public, as well as paid performances.

I left my city a long time ago. Not sure where to go but what’s more important is that you dress and act how you choose and enjoy the night with your bride. Screw what other people think. When you spend time with the one you love then not much else matters. And it always felt nicer to me to play dress up.
Just Enjoy!