I read something years ago (pre-internet) don't know how much truth there was to it, but it advised that it it was best to have 2 pairs of shoes with different heel heights and alternate the two---better for your spine somehow. So that's kind of what I've followed ever since, along with investing in shoes that were good quality if they are ones I plan to have around for a long time. That being said, the most comfortable boots I ever had was a $12.95 pair of northwest territory from kmart I got for working in the dirt. I tried to go back and buy another pair after I realized how great they were but the style had changed. I wore the heck outta those boots everywhere for about 15 years---I finally had to part with them after the sole cracked wide open. Geez I miss those boots!
Back in my parents' day if you could afford it then you had one pair of shoes for everyday and a separate pair for church.
After 1 or 2 pair, then it's a matter of personal want/needs, though I think having a pair of "shower shoes" is a good idea for anyone who's going to be using public showers.
Like so much of wheel life, the answers will be highly individual. If you have them already and have room, take a few of your favorites until you find what works for you. If you don't already have them then it depends on how you are planning to live the lifestyle---good quality hiking/walking shoes of some kind would be what I would choose if I could only choose one pair.
