I can’t help you much on casual boots as my experience is mostly hunting, backpacking, mountaineering, but Redwings are a quality boot, hard to go wrong there.
I’m on a second pair of all leather 8” tall Danner Santiam hunting boots with their Danner Bob outsole, the quietest outsole I’ve walked on in the forest and field, I wore the old ones through 17 seasons and the new through the past 6, I highly recommend them for walk/stalk-type hunting. For hiking I have a light weight pair of Merrell Moab II’s and for backpacking I have an old trusted pair of all leather 6” tall Asolo TPS GV’s w/a Vibram outsole. I don’t mountaineer any longer but when I did I trusted upon Asolo mountaineering boots.