"2. Secondly, I remember my father wore the standard, pleated, wing tiped shirt with black bow tie. I prefer the winged-tip shirts in this instance. Would that be acceptable? I would obviously wear a black cummerbund with this due to hot weather."
A good place to start is proper terminology. There is no such thing as a " wing tiped shirt". Wing Tips are shoes,
otherwise known as "brogues". A Wing-collared shirt or a shirt with a "wing collar" is what you mean.