There's a surprising amount of research into walking barefoot

I'm a runner and there's a longstanding debate among runners over the right level of padding in shoes. There's a lot of research into barefoot/minimal running versus traditional running shoes.

As the comments suggest, walking barefoot will lead to heavily callused feet not altogether different from hobbits.

Pro: greater damage resistance. Thicker soles mean you can walk across tough surfaces with less of a risk of injury. According to a study in the journal Nature, "people [...] who frequently walk barefoot have thicker and harder calluses than those who typically use footwear." So you already have a real world example.

Con: none. The key finding from that study was that people with these thick calluses do not experience a loss of sensitivity when walking compared to people who wear shoes. (I'm specifically referring to having thick soles, not on the choice to go barefoot. FWIW I still run in traditional running shoes.)

Nothing we don't already have

My father hates shoes and as a result has hobbit feet already. Pros is the savings on footware. Cons are the cracked heels and when he does have to wear shoes, finding a shoe that fits is impossible and has to be custom made.

Basically we already have thick leathery soles like hobbits already and it's shoes that keeps it in check.