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.