If your friend is THAT destitute that he won't buy a pair of black shoes then get him a pair from Payless!
I would go with long ties instead of bow ties...this way the grey tuxes can look like a Morning Suit hybrid. It's the best you can do with what you are working with.
Perfect, so my final questions would be since we are treating these like suits, does this open up the color range for the ties, or should I still stick with the traditional wedding tie look? Just worried that the typical gray on white shirt on charcoal suit might look a little bland.