Foxy, and others, have in the past recommended Katrina's in Docklands. I have no first-hand experience.
More difficult, but can be done. So-called "butcher's stripes" can work well with CBD attire i.e. dark suits. Pale pink, lavender and such can be OK with darker complexions. Palefaces like me should generally avoid them. I note that you rarely if ever wear ties (at least in the fits you post), so patterned shirts might work with plain jackets - but they should be cut to work without a tie. For instance, button-downs.
OK, so that's my advice dispensed for the day. Now I would like to solicit some.
Can anyone recommend a good deli or supermarket focused on Italian groceries, preferably in the inner-city area? I used to shop at Norton Street Grocer in Bondi Junction, but they have tragically closed. It's hard for me to get to Leichhardt as I don't have a car.
I've searched high and low in the CBD for delicacies such as cotechino sausage and papardelle, and simply can't find them. Even David Jones food hall was of no use.