Second the Alden Indy recommendation. I’ve had a mountain of Red Wings (and other American made boots) and nothing is as comfortable (for me) as the Indy.
$250 isn't much to work with for a decent boot these days. He also said he doesn't want laces. I admit I'm kind of at a loss there since I don't do cowboy boots or Chelseas.For those of you recommending the Alden Indy- please advise when it can be consistently sourced for the OPs clearly stated budget of 250USD USED or New.