It depends a bit on the climate where you live. Assuming you get rain and snow in the winter, and you'll start this autumn, I'd suggest you start with rubber soled shoes.
In my opinion, a good starter wardrobe would be something like:
3 lighter colored leather soled shoes for spring/summer
1 pair of black oxfords for formal wear
2 rubber soled shoes for spring/autumn
2 rubber soled boots for autumn/winter
...something like that.