In the mail came these. Interesting configuration and style. They're rugged and athletic. They look from the turn of the century, yet with new features.
It has a feel of newer Clark's type shoes. Sort of bootish but not, a little more sporty than in the 70s, and there you have it. A modern classic. When would I wear them in the question. I almost feel like it's for travel, when you'd take just one pair of shoes to do everything.
I put it up on HB blog.