They're both frye boots. I might have to get the one on the left. It fits all my criteria and their stuff is awesome.
The left is the frye james and right is the frye philip. I think they have different versions of each one with lugged soles vs leather soles vs brown leather vs distressed leather, etc. Those are the combinations I like best because they can look professional while still take a beating and go well with jeans for a night out!