[Kath]

I was reading the Prologue bit of Fotr just yesterday and it said that Hobbit's very rarely wear shoes due to having very thick soles and a thick covering of hair like that on their heads. Now it seems unlikely that this would have developed due to living in the Shire as it is grassy and kind on the feet.

My theory is that these features developed during the time when they lived in harsher terrains. Therefore the members of the Fellowship would not need shoes as while they were not used to walking on rough or rocky land their feet still had these defences against it.