Agree with the Iron Rangers, I tell my wife that they are my outdoor slippers. I had zero problem with break in. Hate crocks / sandals especially if I'm on a plane and the guy next me has his yellow fungus toenails showing.Red Wing Iron Rangers - I always hear people complaining that these are uncomfortable, but for me, these are the most comfortable boots on the planet (after the required initial break-in period, of course); I've got a pair in brown, and another one in black.
My other favorite shoes a specific model of Clarks wingtips - I found these a few years ago, they were so comfortable that I bought a couple of pairs in brown and black, saving some in a closet, until the first pair is worn out (took about 6 or 7 years).
My favorite hiking boots at the moment are Salewas, but I get whatever fits my requirements, not stuck on a specific brand.
I hate a too casual look (don't even get me started on the hippie slob look - looking at you, Birkenstocks & Crocs), so I don't wear sneakers/tennis shoes/trainers - unless it's for actual sporting activities ,(I do wear some at the gym); but for very hot summer days I've got a pair of low-top cotton sneakers...