I own 10-12 pairs of shoes but when I travel, I usually take only one. In a last minute decision, I always grab a pair that I rarely wear.
When I moved to Ethiopia for the better part of a year, I brought only a pair of Soaps (so called "freestyle walking" shoes): not a brilliant move as there are no handrails and about as many curbs.
When I went to India a couple years later, I inexplicably brought my Soaps again: this time complete with holes in the bottoms.
Now I'm in Italy with only a pair of $9, fake-leather, not very comfortable, shoes.
Next time I travel, I'm going to delegate the shoe-choosing decision to a trusted friend.