For the record, I went with some boots from Chippewa. American made, union made, right here in Missouri. Since I got them, I've noticed them a few different times in film, though not as often as I see Red Wings, Doc Martens or Alden's "Indy Boot." I'm surprised that this was a "thing" that I was completely unaware of. I even saw them on the Walking Dead (I forgot which character.) Oh, and I also noticed Louis C.K. wearing a pair on a stand-up routine.
They were not very comfortable at first, but I am slowly breaking them in. I wore some cheap boots as a carpenter and they sucked. Then I went with a better-but-still-less-than-a-hundred-dollar boots and while they were nothing special, but they were fine; a lot better than the cheaper pair. I didn't need to break them in, they were fine right out of the box. I also wore the standard issue boots in the Army (this was when they were black and you had to polish them) for a year and they sucked. I bought some jump boots and those were remarkable; once again, right out of the box.
I even had a pair of Doc Martens that I tended bar in for a while. They were a size too big, but they were on the Clearance rack and I needed a pair for work; cheaply.
So I've worn my fair share of boots. But I never had a pair that I had to "break in." But these are almost there and I'm starting to get why people say that a good pair of boots are more comfortable than sneakers. I always thought that was bull-****.