In the winter, Red Wing gore tex insulated, warm and dry feet in a Maine winter makes a rather large difference in ones day. In the summer, New Balance. In fact I just got back from the New Balance tent sale. 300 plus dollars later for a family of large fat feet New Balance rules for footware especailly when you wear a 16 4E
Real work shoes generally work best for me. Here are some thoughts: -I prefer slip-on to lace up boots. My lace-ups typically end near the ankle (mid-rise). -A very stiff shank, as found in many "coyboy" boots, is very comfortable if your work has you either standing on concrete, or up on a ladder all day. -Steel toes can be cold in winter. -Summer boots need to breath a lot. Look at the leather/fabric combos. -Rough job sites call for boots with some serious sole tread! -Sneakers- especially the "Vans" or 'skateboard' type, work well in offices, and for crawling around.
Finally, have at least two pair, and switch off daily.