New shoes if I am going on a real vacation.
One pair brown, one black and sneakers.
Going to China and Japan this summer and will pack 1 new pair black bally oxford, 1 pair brown Santorini loafer, and will wear Mizuno Wave Creation (with Thorlo socks).

Brown for casual/sport
Black for evening/dressy
Mizuno for comfort, heavy walking and work-outs

New Balance 999s (made in america also a good bet, but heavier)

Ecco and Mephisto also good for comfort walking.