Beat-to-death CG penny loafers, because it occurred to me that I could buy boat shoes, or I could spend the same scratch and get a new pair of penny loafers/cycle down my old ones.
I also have a pair of bad-taste tassel mocs with a missing tassel and a fake-gator vamp. They're comfortable, though.
White, American, young, poor. Two of those I'm stuck with, one of those I wish I could keep, and one I'll give up at the drop of a hat. Still gonna wear loafers without socks when I wear shorts, because if I'm wearing shorts, I'm basically in "I'd rather be naked but I'm too polite and might have to sit on something hot" mode.
Some five or six year old Sperry Gold Cup boat shoes. Other than a couple of eyelets coming loose, they appear to be indestructible and are comfortable as all get out. Those or my Keen H2O's.
The only silver lining to our puppy chewing up my ancient LL Bean moose hide house shoes is that it removed the temptation to put them on to run down to the post office or corner gas station.