I love the look of these boots by Allsaints: http://www.us.allsaints.com/men/footwear/allsaints-hazard-boot/?colour=29&category=315
But the quality is allegedly pretty poor. A lot of lower end shoe manufacturers also make "Trench boots" or whatever this style is called, but it seems to be an area that is lacking when it comes to brands in the $300 range. Some boots that come to mind that people have suggested to me that don't quite meet this aesthetic: Non W+H Dayton Boot, Iron Ranger, Katahdin, OSB trench boot, 1000 mile boot, Frye boots (ugly, ugly distressing, apparently still some PQ issues)
I like the slimmer profile- it reminds me in particlar of the W+H Service Boot. Some higher end brands come to mind (Fiorenti + Baker 745 workboot) but their boots are a limited run and usually I can't find them in brown.