[Stillwater]

It'd be boat shoes and rubber-soled loafers for me.

 

[Stillwater]

Really? You could walk around all day in loafers? I could not.

Loafers for evenings and travel days. For walking around Barcelona and Cannes I'd wear something like these: Men's Boat Shoe | Marine | Clovehitch II | Brown Cinnamon | Sebago – Sebago-USA

There are lots of comfortable chukkas with walking soles that look good. If Chelsea boots I'd probably compromise and wear Blundstones or similar. Not the same thing I know.