Are you replacing the whole sole or just the heel? If you walk a lot, it's not unnatural to have to replace the toplift; however, if you are wearing through the sole to the point that a hole develops in the ball area of the sole, then you're putting on some miles there.
Hopefully you have at least a couple other shoes in your rotation as the tan will be memorable to people and you want to at least have a decent rotation. The former is "dressier" since it has less broguing. The Strand is an AE favorite so they will likely get the popular vote.
Both are fine shoes; I like the last of the Clifton better though (never a fan of the 5 when I wore AE).