My personal favorite boots I ever owned, were the Doc Marten's Air Wear that I got in like 8th grade? Paid 450 dollars for them, but at the time I didn't have bills so it wasn't a big deal. I wore them a lot. Every shitty fast food job, it was fine, given they were oil and fat and chemical resistant and all that. I called them my Frankenstein Boots, because they had a "squared" tip near the toes, which reminded me of the movie monster. I still had them until about 5 years ago. In law tossed them in the trash while I wasn't there. They were OLD. I wore them all the time and loved them though, and, even though they cost a bit, I did get over 20 years out of them, so I can't complain too much.