We used to get real deal surplus Vietnam Jungle boots for $5.00 a pair when I was a kid, I wore them all the time.
For riding I just wore out a pair of Sidi On Road Sympatecs, I loved em but after 5 years of wearing them on the bike to work, then working in them all day they're pretty well hammered. Since I spent a lot of money in the last few months on the Aerostitch, new helmet and the Bandit (thank God I didn't need a battery!) I didn't want to spend another $280 on boots so I got some good ol' lug sole, steel toe Chippewa Engineer boots. I know they're not the best for riding but I've worn 'em for years and I like 'em just fine.