Hi Leo,
Yes, that’s indeed quite challenging.
Years ago, I wanted to do something ‘similar’ and tried all sorts of techniques. At the end I used not 1 piece of ‘cloth’, but small patches, and ‘stitched them toghether where needed. This was based on the fact, that there is quite a bvit of ‘cloth’, that is not visible, where it goes under itself. So, I mean something like this:

Theoretically, it should be possible with a Cloth Sim, but that’s gonna be a lot harder to get right (believe me, I tried😉)