YA TU have you tried that though? I have wanted to do that with some of those Keen sandals. They have a pretty firm soles, and I think they are deep enough, but come to think of it, I don't think they have an insole.

I wanted to point out though, Chucks are going to be really squishy, to the point that unclipping may tear out the cleat. But then, I haven't tried it.