Those aren't chukkas (which are boots), those are beat-up glued together black plain-toe bluchers on a rather squarish last -- cop shoes. I had a pair like that in high school -- Nunn Bush (former employer of John Wayne Gacy) -- and I think they came from Sears? They always seem to have them at the MJM near me, but I don't know if that's a chain you can get to.
Probably what I had:
They held up okay. If I polished them up, I could probably wear them now, but I wouldn't.