I've tried something similar. The results weren't perfect, but there are a few things that might help: - Make sure that the belt is double-sided. The inside of the belt should have its normals facing the tabard. - You could try modeling the belt closely around the tabard in frame 1 and have it shrink to fit the figure in the end frame. Then you can try to constraining vertices in the tabard to the belt. - Since the belt has rather sharp edges, it might be a good idea to enable the "object vertex against cloth polygon" and "object polygon against cloth polygon" options. Maybe increase the amount of calculations per step from 2 to 4 or 5. Good luck!

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