Hi nopopoch,
I'm often torn between simulation/dynamics and manual animation. Hence, I checked which one might work better. Sometimes it is a mix.
The main question would be whether splitting the headband into three parts would be the better solution. Inside the Hard-Plastic elements, perhaps just a modeled strap part is static.
As a side note, the hard plastic parts may need some attention. Optimize them to get it in one piece, then use the Remesher and have for each object. They can't be connected as one object if they need to float in space.
I have set up two simplified scenes.
Each uses a Vertex Map to define areas with more or less bendiness.
The idea in the file "02" was to use the Connector as stabilization based on two elements that will not be shown.
A torus here represents the Hard Plastic part. I'm not confident that this is the best way to go. I see it as "swimming".
The file "11" also used the stabilization square as a Belt base. I have used just a Vibrator Tag here to create the motion.
This allows for a more direct art direction, which is a priority for me. But yes, the band itself works as well as Cloth.
Here are the two files; I'm sure there are a few more options and combinations. But I hope that helps you find your favorite setup.
https://stcineversityprod02.blob.core.windows.net/$web/Cineversity_Forum_Support/2024_PROJECTS_DRS/20240222_CV4_2024_drs_24_SLhb_02-11.zip
All the best