IMO tall wheels and rubberband tires look ghetto and I think anything taller than 17" ruins the look of a classic car. What's more, it works against any lowering, meaning that you will have to lower more radically and possibly create more wheelwell height to get the same lowness. And then there's the steering clearance to consider!
If you REALLY like the tall stuff and it culturally suits you, it might be better to sell your 57 to someone with classic taste and go get yourself a Hummer