As a lurker of both /fa/ and /out/ I feel I should point out how ridiculous you'll look walking down a city street in OP's shoes. A principle of both /fa/ and /out/ is that you should dress appropriately for the occasion. That is to say, do not wear Allen Edmonds Dalton boots on a multi-day hike, and do not use your ALICE pack as a school backpack.
Nevertheless, there are plenty of nice looking clothes that you can take /out/. I would call these "traditional work wear." Other than the Wolverine 1000 mile boot mentioned above, I'd recommend the Red Wing Iron Ranger (pic related). Both of these boots are more or less unchanged from their blue collar origins. Another contender for those on a budget would be the LLBean Katahadin Iron Works Engineer Boot.
http://www.wolverine.com/US/en/1000MileCollectionhttp://www.redwingheritage.com/boots/#&m=/detail/8111-heritage-us/8111-red-wing-heritage-mens-iron-ranger-boot-amber/http://www.llbean.com/llb/shop/49464?page=mens-katahdin-iron-works-engineer-boots 